TW200413400A

TW200413400A - Lipid a derivatives which have glucose back-bone as the reducing sugar part

Info

Publication number: TW200413400A
Application number: TW092136470A
Authority: TW
Inventors: Masao Shiozaki; Takaichi Shimozato; Yukiko Watanabe; Takashi Mochizuki
Original assignee: Sankyo Co
Priority date: 2002-12-24
Filing date: 2003-12-23
Publication date: 2004-08-01
Also published as: WO2004058788A1; AU2003289493A8; AU2003289493A1

Abstract

A compound of the formula (I): [Q is oxygen atom, C1-C3 alkylene group, yl-O-Alk-or yl-O-Alk-O-(Alk is C1-C3 alkylene group), R1, R2 and R4 are the same or different, each is hydrogen atom, C1-C20 alkyl group which may be substituted, C2-C20 alkenyl group which may be substituted, C2-C20 alkynyl group which may be substituted, C1-C20 alkanoyl group which may be substituted, C3-C20 alkenoyl group which may be substituted or C3-C20 alkynoyl group which may be substituted, R3 is C1-C20 alkanoyl group which may be substituted, C3-C20 alkenoyl group which may be substituted or C3-C20 alkynoyl group which may be substituted, R5 is hydrogen atom, halogen atom, hydroxy group, C1-C6 alkoxy group which may be substituted, C2-C6 alkenoxy group which may be substituted or C2-C6 alkynoxy group which may be substituted] or the pharmaceutical acceptable salts thereof.

Description

玖、發明說明【發明所屬之技術領域】本發明爲有關具有優異噬菌體活性抑制作用，可作爲抗炎症劑’抗自體免疫疾病劑，免疫抑制劑，冠狀動脈旁路形成術後預後改善劑或抗敗血症劑之新潁脂肪質A同類物或其樂理容許鹽，含其爲有效成分之醫藥組成物，使用該脂肪質A同類物或其藥理容許鹽以製造該醫藥組成物，或投予藥理有效量之該脂肪質A同類物或其藥理容許鹽至温血動物（特爲人）以預防或治療疾病之方法。【先前技術】來自腸内細菌之革蘭氏陰性菌細胞壁的最表層中含不分泌至菌體外之毒成分（内毒素），該内毒素，除内毒素活性以外，亦顯示與活體自己防禦有關之免疫佐劑活性作用，噬菌體活性化作用，促細胞分裂劑活性作用，發熱作用 ’腫瘤壊死作用，抗體産生増強作用，T N F誘導作用等各種生物活性。該内毒素由脂多糖而成，已知和所謂稱爲脂肪質A的部分爲内毒素活性的活性中心（井本等，Tetrahedron · Letters，1 985 年，26 巻，P · 1 545 )。另外，作爲細菌脂肪質A相關化合物自Rhdobacter sphaeroides發現之化合物（Rs-DPLA)(古列西等， Journal · of· biological · Chemistru，1988 年，263 巻，p • 5 5 0 2 ； Infcetion· Immunity，57 巻，P · 1336)，對人噬菌體顯示LPS拮抗體活性，有可作爲抗自體免疫病劑或 200413400 抗敗血症劑使用之可能，而進行硏發顯示和噬菌體活性化作用相反之抑制作用的藥劑。基於該結果，頻繁嘗試合成具有上述各種活性中有用活性之化合物之衍生物，已知例如，C h 1· i s t等，J 〇 u r n a 1 〇 f America Chemical · Society，116 巻，P · 3637;特開平 10-3 246 94號公報；特開平5_i 94470號公報；特開200 1_ 34 8 3 9 6號公報；或US P 5 935938號公報記載之衍生物。【發明內容】本發明者等課題爲硏發具有優異噬菌體活性抑制作用，鲁可作爲抗炎症劑，抗自體免疫疾病劑，免疫抑制劑，冠狀動脈旁路形成術後預後改善劑或抗敗血症劑之新穎脂肪質 A同類物。本發明者等爲解決上述課題，致意努力之結果，發現1 位有膦酸基或膦酸氧乙基之葡糖基脂肪質A同類物系統之化合物，具有優異噬菌體活性抑制作用，而完成本發明。本發明化合物如下化合物或其藥理容許鹽： 1) 一般式 _说明 Description of the invention [Technical field to which the invention belongs] The present invention relates to an excellent phage activity inhibitory effect, and can be used as an anti-inflammatory agent, an anti-autoimmune disease agent, an immunosuppressive agent, a prognostic improver after coronary artery bypass formation, or An antiseptic agent of a neolipid A homologue or its permissible salt, a medicinal composition containing it as an active ingredient, using the fatty A homologue or its pharmacologically acceptable salt to manufacture the medicinal composition, or pharmacology An effective amount of the fatty A analogue or a pharmacological method that allows salt to warm-blooded animals (especially humans) to prevent or treat diseases. [Prior art] The outermost layer of the cell wall of Gram-negative bacteria from intestinal bacteria contains a toxic component (endotoxin) that is not secreted to the outside of the bacteria. In addition to endotoxin activity, the endotoxin also shows its own defense against the living body Related biological activities such as immune adjuvant activity, phage activation, mitogenic activity, fever 'tumor death, stubborn antibody production, TNF induction. This endotoxin is made of lipopolysaccharide, and the part known as fatty A is known as the active center of endotoxin activity (Imoto, et al., Tetrahedron · Letters, 1 985, 26 巻, P · 1 545). In addition, as a compound related to bacterial fat A found from Rhdobacter sphaeroides (Rs-DPLA) (Gullish et al., Journal · of · biological · Chemistru, 1988, 263 巻, p • 5 5 0 2; Infcetion · Immunity (57 巻, P · 1336), showing LPS antagonistic activity against human phage, which may be used as an anti-autoimmune agent or 200413400 anti-septic agent, and the suppression effect of eruption display and phage activation is opposite Pharmacy. Based on this result, attempts have frequently been made to synthesize derivatives of compounds having useful activities among the various activities mentioned above. For example, C h 1 · ist, etc., J 〇urna 〇f America Chemical · Society, 116 巻, P · 3637; Japanese Patent Publication No. 10-3 246 94; Japanese Patent Publication No. 5_i 94470; Japanese Patent Publication No. 200 1_34 8 3 9 6; or derivatives described in US Patent Publication No. 5 935938. [Summary of the invention] The present inventors and other subjects have excellent phage activity inhibitory effect on hair. Luco can be used as an anti-inflammatory agent, anti-autoimmune disease agent, immunosuppressive agent, prognostic improver after coronary artery bypass formation or anti-septicemia. The novel fatty A analogue of the agent. In order to solve the above-mentioned problems, the present inventors have paid tribute to the results, and found that a compound having a glucosyl fatty A homologous system having a phosphonic acid group or phosphoethyloxyethyl group at the 1-position has an excellent phage activity inhibitory effect, and completed the present invention. invention. The compounds of the present invention are the following compounds or their pharmacologically acceptable salts: 1) General formula _

〔式中， Q爲氧原子，C 1 — C 3伸烷基，基- 0-Alk-或基-〇_Alk_ 〇-(但’ Aik爲Ci—C3伸燒基）， R1，R2及R4爲相同或不同，各爲氫原子，可有選自下 200413400 述取代基群A之一種以上基取代之C ! 一 C 2〇烷基，可有選自下述取代基群A之一種以上基取代之C 2 — C 2〇烯基，可有選自下述取代基群A之一種以上基取代之C 2 - C 20炔基，可有選自下述取代基群A之一種以上基取代之C , 一 C 20 烷醯基，可有選自下述取代基群A之一種以上基取代之C 3 - C 2〇烯醯基或可有選自下述取代基群A之一種以上基取代之C3 — C2G炔醯基’ R 3爲可有選自下述取代基群A之一種以上基取代之C ! - C 2〇烷醯基，可有選自下述取代基群A之一種以上基取代之C 3 — C 2Q烯醯基或可有選自下述取代基群A之一種以上基取代之C 3 - C 2 0快釀基’ R5爲氬原子，鹵原子，羥基，可有氧基之（：！一06烷氧基，可有氧基之C2— C6烯氧基或可有氧基之（：2— 06炔氧基，取代基群A爲鹵原子，羥基，氧基，可有氧基之Ci—C 20院氧基，（C 1— C2Q院氧基）C 1— C2Q院氧基，{ (C 1 — C20院氧基）Ci— C20院氧基} Cl — C2Q院氧基，可有氧基之C2 - C2〇嫌氧基’可有氧基之C2 - c2Q炔氧基，可有興基之Cl — C2〇院醯氧基’可有氧基之C3 — C20燃醯氧基，可有氧基之C3 - C2〇炔醯氧基及Ci〜院磺醯基〕。本發明化合物（I )中，宜爲， 2 ) R 1爲可有選自取代基群A取代基之取代c 4 一 C 18院基或C4— Ci8燒基’ 200413400 3 ) R 1爲可有選自取代基群a取代基取代之C 4 一 C i8烷基， 4 ) R 1爲可有選自取代基群A取代基取代之C 8 - C i8烷基或C8 — Ci8烯基， 5 ) R 1爲可有選自取代基群A取代基取代之C 8 - C !8烷基， 6 ) R 1爲未取代或有選自取代基群a中羥基或氧基爲取代基取代之C1G—C18烷基或C1()— C18烯基， 7 ) R 1爲未取代或有選自取代基群A中羥基或氧基爲取代基取代之C i - C ! 8烷基， 8 ) R 1爲未取代或有選自取代基群A中羥基或氧基爲取代基取代之癸基，十二基，十四基，十二碳烯基或十四碳烯基， 9) R1爲未取代或有選自取代基群A中羥基或氧基爲取代基取代之癸基，十二基或十四基， 1 〇 ) R 2爲可有選自取代基群A取代基取代之C 4 一 C i 8 烷基或C 4 一 C ! 8烯基， 1 1 ) R 2爲可有選自取代基群A取代基取代之C 4 一 C ! 8 烷基， 1 2 ) R 2爲可有選自取代基群A取代基取代之C 8 — C ! 8 烷基或C8—C18烯基， 1 3 ) R 2爲可有選自取代基群A取代基取代之C 8 — C ! 8 烷基， 1 4 ) R 2爲未取代或有選自取代基群A中羥基爲取代基取 -10- 200413400 代之C1G—Cl8院基或C1()—Cl8烯基， 1 5 ) R 2爲未取代或有選自取代基群A中羥基爲取代基取代之ClQ— Cl8院基， 1 6 ) R 2爲未取代或有選自取代基群A中羥基爲取代基取代之癸基，十二基，十四基，5 —十二碳烯基或7 -十四碳烯基， 1 7 ) R 2爲未取代或有選自取代基群A中羥基爲取代基取代之癸基，十二基或十四基， 18) R2爲未取代C ίο— C 18院基， 19) R2爲未取代癸基，十二基或十四基， 20) R3爲未取代C 8- C is綜釀基， 21) R3爲未取代（31() - C18烷醯基， 22) R3爲甲醯基，乙醯基或丙醯基， 23 ) R 3爲甲醯基或乙醯基的化合物， 24) R 4爲可有選自取代基群A取代基之C 4一 C18烷基或C4 一 Cl8燃基’ 25) R 4爲可有選自取代基群A取代基取代之C 4一 C18 院基’ 26) R 4爲可有選自取代基群A取代基取代之C 8— C! 8. 烷基或C8— C18烯基， 27) R4爲可有選自取代基群A取代基取代之C8—C1S 烷基， 28 ) R 4爲有選自取代基群A之氟原子，羥基，未取代C 12— C 14院氧基’未取代C 12 - C 14燦氧基，未取代C 12 - 200413400 C ! 4院釀氧基或未取代c ! 2 — C i 4烯醯氧基爲取代基取代之c 1G— c 18院基或C 1Q一 C 18烯基， 29 ) R 4爲有選自取代基群A之氟原子，羥基，未取代C 1 2 一 C 1 4院氧基’未取代C ! 2 - C 1 4烯氧基，未取代C i 2 — C i 4院酸氧基或未取代c ! 2 — C i 4烯醯氧基爲取代基取代之C IQ— C 18院基，[In the formula, Q is an oxygen atom, C 1 -C 3 alkylene, -0-Alk- or -0_Alk_〇- (but 'Aik is Ci-C3 alkyl), R1, R2, and R4 Are the same or different, each is a hydrogen atom, and may have one or more C! -C20 alkyl groups substituted with one or more groups selected from the substituent group A described below in 200413400, and may have one or more groups selected from the following substituent group A The substituted C 2 -C 2 0 alkenyl group may have a C 2 -C 20 alkynyl group substituted with one or more groups selected from the following substituent group A, and may be substituted with one or more groups selected from the following substituent group A The C, -C 20 alkylfluorenyl group may have a C 3 -C 2o alkenyl group substituted with one or more groups selected from the following substituent group A or may have one or more groups selected from the following substituent group A Substituted C3-C2G alkynyl'R 3 is a C! -C2O alkyl group which may be substituted with one or more groups selected from the following substituent group A, and may have one selected from the following substituent group A The C 3 -C 2Q alkenyl group substituted with the above group may have a C 3 -C 2 0 fast-substituted group substituted with one or more groups selected from the following substituent group A. R 5 is an argon atom, a halogen atom, a hydroxyl group, may be Aerobic (:! 06 alkoxy C2-C6 alkenyloxy which may have an oxy group or (2- 06 alkynyloxy group which may have an oxy group, the substituent group A is a halogen atom, a hydroxyl group, an oxy group, and a Ci-C 20 group which may have an oxy group Oxygen, (C 1- C2Q-oxyl) C 1- C2Q-oxyl, {(C 1- C20-oxyl) Ci- C20-oxyl} Cl — C2Q-oxyl, C2 with oxygen -C2〇 alkoxy 'can be oxy C2-c2Q alkynyloxy, can have Xingji's Cl — C2〇 courtyard oxy' can have oxy C3 — C20 alkoxy, can have oxy C3-C2O alkynyloxy and Ci ~ sulfonyl)] In the compound (I) of the present invention, preferably, 2) R 1 is a substituent c 4 -C which may have a substituent selected from the substituent group A 18 courtyard or C4—Ci8 alkyl group '200413400 3) R 1 is a C 4 -C i8 alkyl group which may be substituted with a substituent selected from the substituent group a, 4) R 1 may be substituted with a group selected from the substituent A Substituted C 8 -C i8 alkyl or C8—Ci8 alkenyl, 5) R 1 is a C 8 -C! 8 alkyl group which may be substituted with a substituent selected from the substituent group A, 6) R 1 is unsubstituted Or a C1G-C18 alkyl group or C1 ()-C1 substituted with a hydroxyl group or an oxy group in the substituent group a 8 alkenyl, 7) R 1 is unsubstituted or substituted with C i-C! 8 alkyl selected from hydroxyl or oxo in the substituent group A, 8) R 1 is unsubstituted or substituted with In the group A, the hydroxyl group or the oxy group is a decyl group, a dodecyl group, a tetradecyl group, a dodecenyl group or a tetradecenyl group substituted with a substituent, 9) R1 is unsubstituted or has a group selected from the substituent group A Wherein the hydroxyl group or the oxy group is a decyl group, a dodecyl group or a tetradecyl group, and 1) R 2 is a C 4 -C i 8 alkyl group or C 4 which may be substituted with a substituent selected from the substituent group A; 1 C! 8 alkenyl, 1 1) R 2 may be C 4 -C! 8 alkyl substituted with a substituent selected from substituent group A, 1 2) R 2 may have a substituent selected from substituent group A Substituted C 8 —C! 8 alkyl or C 8 -C 18 alkenyl, 1 3) R 2 is a C 8 —C! 8 alkyl group which may be substituted with a substituent selected from the substituent group A, 1 4) R 2 is Unsubstituted or selected from the substituent group A. The hydroxyl group is substituted by -10- 200413400 and substituted by C1G—Cl8 or C1 () — Cl8 alkenyl, 1 5) R 2 is unsubstituted or has a selected group In the group A, the hydroxyl group is a ClQ-Cl8 group substituted by a substituent, 1 6) R 2 is unsubstituted or has In the substituent group A, the hydroxy group is a substituted decyl group, dodecyl group, tetradecyl group, 5-dodecenyl group or 7-tetradecenyl group, and 1) R 2 is unsubstituted or selective. From the substituent group A, the hydroxy group is a substituted decyl group, a dodecyl group or a tetradecyl group, 18) R2 is an unsubstituted C 18-C18 group, 19) R2 is an unsubstituted decyl group, a dodecyl group or Tetradecyl, 20) R3 is an unsubstituted C 8-C is synthetic group, 21) R3 is unsubstituted (31 ()-C18 alkylfluorenyl, 22) R3 is formamyl, ethenyl or propionyl 23) A compound in which R 3 is methyl or ethyl, 24) R 4 is a C 4 -C 18 alkyl group or a C 4 -Cl 8 alkyl group which may have a substituent selected from the substituent group A 25) R 4 is C 4 -C18 may be substituted with substituents selected from substituent group A 26) R 4 is C 8-C! 8 alkyl or C8-C18 olefins substituted with substituents selected from substituent group A 27) R4 is a C8-C1S alkyl group which may be substituted with a substituent selected from the substituent group A, 28) R4 is a fluorine atom, a hydroxyl group, and an unsubstituted C12-C14 group selected from the substituent group A Oxy 'unsubstituted C 12-C 14 canoxy, unsubstituted C 12-200413400 C! Or unsubstituted c! 2 —C i 4 alkenyloxy is a substituted c 1G— c 18 alkyl or C 1Q—C 18 alkenyl, 29) R 4 is a fluorine atom selected from substituent group A , Hydroxy, unsubstituted C 1 2 -C 1 4 alkoxy 'unsubstituted C! 2-C 1 4 alkenyloxy, unsubstituted C i 2 —C i 4 acyloxy or unsubstituted c! 2 — C i 4 alkenyloxy is C IQ—C 18

30 ) R 4爲有選自取代基群A之氟原子，羥基，未取代c 12 - C ! 4院氧基或未取代^ ! 2 一 c i 4烷醯氧基爲取代基取代之〔1()— Ci8院基， 3 1 ) R 4爲有選自取代基群a之氟原子，羥基，未取代C 12— C μ烯氧基或未取代c 12一 C μ烯醯氧基爲取代基取代之〔1()— Ci8院基， 32 ) R 4爲有選自取代基群a之氟原子，羥基，未取代C 12〜C ! 4烷氧基或未取代C ! 2 一 C , 8烯氧基爲取代基取代之 C 1。— C 1 8 院基，30) R 4 is a fluorine atom selected from the substituent group A, a hydroxyl group, unsubstituted c 12 -C! 4 alkoxy or unsubstituted ^! 2-ci 4 alkyl alkoxy is substituted by a substituent [1 ( ) — Ci8, 3 1) R 4 is a fluorine atom selected from the substituent group a, a hydroxyl group, an unsubstituted C 12- C μalkenyloxy group or an unsubstituted c 12-C μalkenyloxy group is a substituent Substituted [1 () — Ci8 courtyard, 32) R 4 has a fluorine atom selected from the substituent group a, a hydroxyl group, an unsubstituted C 12 ~ C! 4 alkoxy group or an unsubstituted C! 2 -C, 8 Alkenyloxy is C 1 substituted with a substituent. — C 1 8 courtyard foundation,

33 ) R 4爲有選自取代基群A之氟原子，羥基或未取代C 12〜C i 4烷氧基爲取代基取代之C ! 〇 — C i 8烷基， 34) R4爲有選自取代基群A之氟原子，羥基，未取代C 12〜C 14烯氧基爲取代基取代之C 1G— C 18烷基， 35) R4爲有選自取代基群A之十二氧基，十四氧基，5 '^十二碳烯氧基，7—十四碳稀氧基，十二院醯氧基，十四烷醯氧基，5—十二碳烯氧基或7-十四碳烯氧基爲取代基取代之癸基，十二基，十四基，5-十一碳烯基或7—十四碳烯基， -12 - 200413400 36) R4爲有選自取代基群a之十二氧基，十四氧基，5 一十一碳燃氧基’ 7—十四碳嫌氧基’十一院釀氧基’十四院醯氧基，5-十二碳烯氧基或7—十四碳烯氧基爲取代基取代之癸基’十一基或十四基， 37) R4爲有選自取代基群A之十二氧基，十四氧基，十二烷醯氧基或十四烷醯氧基爲取代基取代之癸基，十二基或十四基， 3 8 ) R 4爲有選自取代基群A之5 -十二碳烯氧基，7 -十四碳烯氧基，5—十二碳烯氧基或7-十四碳烯氧基爲取代基取代之癸基，十二基或十四基， 39) R4爲有選自取代基群A之十二氧基，十四氧基，5 一十二碳稀氧基或7-十四碳烯氧基爲取代基取代之癸基，十二基或十四基， 40) R4爲有選自取代基群A之十二氧基或十四氧基爲取代基取代之癸基，十二基或十四基， 41) R4爲有選自取代基群A之5-十二碳烯氧基或7 — 十四碳烯氧基爲取代基取代之癸基，十二基或十四基， 42) R5爲鹵原子，羥基或未取RC!— C6烷氧基， 43) R5爲氟原子，羥基或甲氧基， 44 ) Q爲氧原子， 45 ) Q爲膦酸乙基， 46)右糖葡萄糖1位爲α位。其中，更較佳化合物爲：膦酸基6—0 — 〔2—去氧一4 一〇—膦酸基一 3—〇一〔 -13 - 200413400 (R) — 3—甲氧癸基〕一6 —〇—甲基_2— 〔（z) — 11 一（十八碳烯醯基）胺基〕一 β— D -吡喃葡糖基〕一 3-〇一癸基一 2 〇〔（R) — 3 一經基十四基〕一 β— D — 吡喃葡糖苷（以下稱爲化合物1 )，膦酸基6—〇一〔2 —去氧一 4一〇—膦酸基—3 —〇一〔 (R) — 3—甲氧癸基〕一6—〇一甲基一 2一〔（ζ) —1133) R 4 is a fluorine atom selected from the substituent group A, a hydroxyl group or an unsubstituted C 12 ~ C i 4 alkoxy group is a substituted C! 〇—C i 8 alkyl group, 34) R 4 is selected Since the fluorine atom of the substituent group A, the hydroxyl group, and the unsubstituted C 12 to C 14 alkenyloxy group are substituted C 1G—C 18 alkyl groups, 35) R 4 is a dodecyloxy group selected from the substituent group A , Tetradecyloxy, 5 ′ ^ dodecenyloxy, 7-tetradecyloxy, 12-dodecylfluorenyloxy, tetradecanefluorenyloxy, 5-dodecenyloxy Tetradecenyloxy is decyl, dodecyl, tetradecyl, 5-undecenyl or 7-tetradecenyl substituted by substituents, -12-200413400 36) R4 is selected from substituted Dodecyloxy, Tetradecyloxy, 5-11-Carbonoxy, 7-tetradecyloxy Carbenyloxy or 7-tetradecenyloxy is decyl'undecyl or tetradecyl substituted with substituents, 37) R4 is dodecyloxy, tetradecyloxy with substituent group A selected ， Dodecyl fluorenyloxy or tetradecyl fluorenyloxy is decyl, dodecyl or tetradecyl substituted with substituent, 3 8) R 4 is a 5-dodecenyloxy group, a 7-tetradecenyloxy group, a 5-dodecenyloxy group, or a 7-tetradecenyloxy group selected from the substituent group A. Substituted decyl, dodecyl or tetradecyl, 39) R4 is a dodecyloxy group, a tetradecyloxy group, a dodecyloxy group or a 7-tetradecyl group selected from the substituent group A Alkenyloxy is decyl substituted with dodecyl, dodecyl or tetradecyl, 40) R4 is decyl substituted with dodecyloxy or tetradecyloxy selected from substituent group A, twelve Or tetradecyl, 41) R4 is a decyl, dodecyl or tetradecyl group substituted with 5-dodecenyloxy or 7-tetradecenyloxy selected from the substituent group A 42) R5 is a halogen atom, hydroxyl group or RC! —C6 alkoxy group, 43) R5 is a fluorine atom, hydroxyl group or methoxy group, 44) Q is an oxygen atom, 45) Q is a phosphonic acid ethyl group, 46 ) The right sugar glucose 1 position is α position. Among them, the more preferable compound is: phosphonate 6-0— [2-deoxy-4—10—phosphonate—3—0 — [-13-200413400 (R) —3-methoxydecyl] — 6-〇-methyl_2- [(z) — 11 mono (octadecenylamino) amino] -β-D-glucopyranosyl] -3-0-decyl-2 0 [( R) — 3 meridyl tetradecyl] — β — D — glucopyranoside (hereinafter referred to as compound 1), phosphono 6 — 0 — [2 —deoxy 4 — 10 — phosphonic acid — 3 — 〇一 [(R) — 3-methoxydecyl] 6-〇-methyl-2 2 [(ζ) —11

一（十八碳烯醯基）胺基〕一 β - D -吡喃葡糖基〕一 3-〇一癸基一 2 —〇一〔（R) —3—羥基十四基〕—a—D — 吡喃葡糖音（以下稱爲化合物2 )，膦酸基6—0 —〔2 —去氧一 4 一〇一膦酸基一 3 —〇一〔 (R) — 3 —甲氧癸基〕一6—〇一甲基一 2一〔（z) — 11 一（十八碳稀醯基）胺基〕一 β— D -毗喃葡糖基〕一 3 — 〇一十二基一2 —〇一〔（R) 一3 —羥基十四基〕一 β— D 一吡喃葡糖苷（以下稱爲化合物3 )，膦酸基6—0 —〔2 —去氧一4一〇一膦酸基—3—〇一〔 (R) —3 —甲氧癸基〕一6—〇一甲基一 2— 〔（Ζ) — 11Mono (octadecenyl) amino group] -β-D-glucopyranosyl] -3-0-decyl-2-0-0 [(R) -3-hydroxytetradecyl] -a- D — glucopyranose (hereinafter referred to as compound 2), phosphonate group 6-0 — [2 —deoxy-4 10—phosphonic acid group 3 —〇— [(R) — 3 —methoxydecane Yl] -6-O-methyl-2 2 [(z) — 11 1 (octadecylfluorenyl) amino]-β-D-pyranoglucosyl] 3-〇12 2-0-[(R) -3-hydroxytetradecyl] -β-D-glucopyranoside (hereinafter referred to as compound 3), phosphonic acid group 6-0-[2 -deoxy-4101 Phosphonic acid group 3- 3-[[R] 3- 3-methoxydecyl] 6-O-methyl-2 2- [(Z) — 11

一（十八碳烯酿基）胺基〕一 β—D —吡喃葡糖基〕—3-◦ 一十二基一 2 —〇一〔（R) — 3 —羥基十四基〕—a— d -吡喃葡糖苷（以下稱爲化合物4 )，膦酸基3 —〇一癸基一 6 —〇一〔2—去氧一4 一〇一膦酸基一 3 —〇一〔（R) — 3 —甲氧癸基〕一6 —〇一甲基一2 一〔（Ζ) -11一（十八5^細釀基）胺基〕一 β— D -啦喃葡糖基〕一 2 —〇一十四基一 a — D — U比喃葡糖音（以下稱爲化合物5)， -14 - 200413400 膦酸基3 —〇一癸基一ό —〇一〔2—去氧一4 —〇一膦酸基一 3一〇—〔（R) — 3—甲氧癸基〕一 6 —〇一甲基—2 一〔（Ζ) - 11一（十八碳烯醯基）胺基〕一 β一 D —吡喃葡糖基〕一 2 —〇一十四基一 β - D 一姬喃葡糖苷（以下稱爲化合物6 )，膦酸基2，3 —二一〇一十二基一6一〇一〔2 一去氧一 ◦一膦酸基一3 — ◦ — 〔（R) — 3 —甲氧癸基〕一 6 —〇一甲基一 2—〔（Ζ) — 11一（十八碳嫌醯基）胺基〕一β —D—P比喃葡糖基〕一 a—D —卩it喃葡糖甘（以下稱爲化合物7)，膦酸基2，3 —二一〇一十二基一 6一〇—〔2—去氧一4 —〇一膦酸基一3 —〇一〔（R) — 3 —甲氧癸基〕一6〜〇一甲基一 2-〔（Z) — 11一（十八碳綠醯基）胺基〕—β 一 D —吡喃葡糖基〕一 β- D -吡喃葡糖苷（以下稱爲化合物8 )，膦酸基2，3 —二一 ◦一十二基一6 —〇一〔2 —去氧一4 —〇—膦酸基—3—〇一〔（R) — 3 —甲氧癸基〕一6—〇一甲基一 2-〔9—(十八醢基）胺基〕一 β— D—Π比喃葡糖基〕一 a — D -卩比喃葡糖甘（以下稱爲化合物9) ’ 膦酸基2，3 —二一 ◦一十二基一6 —〇一〔2 —去氧一4 —〇一膦酸基一3 —〇一〔（R) — 3 —甲氧癸基〕一6 —〇一甲基一 2一〔9一（十八醯基）胺基〕一 β— D —吡喃葡糖基〕—β — D -吡喃葡糖苷（以下稱爲化合物1 〇 )，鱗酸基2’ 3 —二一〇一十一基一6—〇一〔2 —去氧一 4 -15 - 200413400 —◦一膦酸基一3 —〇一〔（R) —3 —甲氧癸基〕〜6〜〇 —甲基一 2—〔（E) — 9—(十八碳烯醯基）胺基〕〜β〜 D —毗喃葡糖基〕一 α — D —吡喃葡糖苷（以下稱爲化么物 11)，膦酸基3—〇一癸基一 6 —〇一〔2 —去氧〜4〜〇〜膦酉允基一3 —〇一〔（R) — 3—甲氧癸基〕一 6—〇—甲基—2 一〔（Ε) - 9一（十八碳烯醯基）胺基〕一β—D〜卩比喃葡糖基〕一 2 - ◦—十四基一 β - D —吡喃葡糖苷（以下稱爲化合物1 2 )，膦酸基3 —〇一十二基一 6 —〇一〔2 —去氧一 4 —〇—膦酸基一3 —〇一〔（R) — 3 —甲氧癸基〕一6 —〇一甲基一 2一〔（ζ) —11—（十八碳烯醯基）胺基〕一 β— D —吡喃葡糖基〕一 2 -〇一十四基一01— D -吡喃葡糖苷（以下稱爲化合物1 3 )，膦酸基3 —〇一十二基一 6 —〇一〔2 —去氧一 4 一〇一膦酸基一3 —〇一〔（R) — 3 —甲氧癸基〕一6—〇一甲基一 2-〔（Ζ) — 11一（十八碳烯醯基）胺基〕一 β - D -毗喃葡糖基〕一 2 - 0 —十四基一 β - D -吡喃葡糖苷（以下稱爲化合物1 4 )， 2—（膦酸氧基）乙基6— 0 —〔2—去氧一 4一 ◦一膦酸基一 3 —〇一〔（R) — 3 —甲氧癸基〕一6 —〇一甲基一 2 一〔（ζ) — 11一（十八碳烯醯基）胺基〕一 β— D —吡喃葡糖基〕一3 —〇一十二基一 2 —〇一〔（R) — 3—羥基十四基〕—α - D —吡喃葡糖苷（以下稱爲化合物1 5 )， -16 - 200413400 2— （鱗酸氧基）乙基6 —〇一〔2—去氧一 4 一〇一鱗酸基一 3 — ◦一〔（R) — 3 —甲氧癸基〕一6 —〇一甲基一2 一〔（Z) - 11一（十八碳烯醯基）胺基〕—β - D -吡喃葡糖基〕一 3 —〇一十二基—2 — 0 —十四基一 α — D —吡喃葡糖苷（以下稱爲化合物1 6 )， 2— （膦酸氧基）乙基6 —〇一〔2 —去氧一 4一〇一膦酸基一 3—〇一〔（R) —3 —甲氧癸基〕一6 —〇一甲基一2 —〔（Ζ) — 11一（十八碳嫌酿基）胺基〕一 β— D —卩比喃葡糖基〕一 2，3—二一〇一十一·基一 α—D —啦喃葡糖甘（以下稱爲化合物1 7 )， 2一（膦酸氧基）乙基6 一 ◦一〔2 一去氧—4 一〇—膦酸基一 3 —〇一〔（R) — 3—甲氧癸基〕一 6 —〇一甲基一2 一〔（Z) — 11一（十八碳條醯基）胺基〕一 β一 D —批喃葡糖基〕—2，3一二一〇一十二基一 β — D —吡喃葡糖苷（以下稱爲化合物1 8 )， 2 —膦酸乙基ό 一 ◦一〔2 —去氧一3 —〇一〔（R) — 3 —甲氧癸基〕—6 —〇一甲基一 2—〔（Ζ) —11— （十八碳烯醯基）胺基〕一 4 一〇一膦酸基一 β— D -吡喃葡糖基〕一2，3—二一〇一十二基一a—D —吡喃葡糖苷（以下稱爲化合物1 9 )， 3— (膦酸氧基）丙基6一〇—丨2 一去氧一 3 一〇一[(R )一 3 一甲氧癸基]一 6 —〇一甲基一 2 — [(Z)— 11 一（十八碳烯醯胺基）]一 4一〇一膦酸基—β— D —吡喃葡糖基丨一 2 ，3—二一〇一十二基一 a— D —吡喃葡糖苷（以下稱爲化 -17 - 200413400 合物2 0 )， 3— （膦酸基）丙基6—〇一 {2 —去氧一 3 —〇一[(R) —3 一甲氧癸基]—ό 一〇一甲基一2 — [(Z) — 11—(十八碳烯醯胺基）]一 4— ◦一膦酸基一 β— D —吡喃葡糖基丨一 2 ，3一二—〇一十二基一 α— D —毗喃葡糖苷（以下稱爲化合物2 1 )， 0一〇一 {2 —去氧一3 —〇一[(R) — 3 —甲氧癸基]—6 一〇一甲基一 2— [(Ζ) — 11—(十八碳嫌醯胺基）]一 4 一〇一膦酸基一β — D —毗喃葡糖基} 一 2, 3 —二一 ◦—十二基一 α- D —吡喃葡糖基甲基二氫磷酸酯（以下稱爲化合物 22)， 6 —〇一{2 —去氧一3 —〇一[(R) — 3 —甲氧癸基]—6 一〇一甲基一2— [(Ζ) — 11—（十八碳烯醯胺基）]一 4 一〇一膦酸基一β — ϋ —吡喃葡糖基丨一 2，3 —二一〇一十二基一 α - D —吡喃葡糖基乙基二氫磷酸酯（以下稱爲化合物 23 )， 6 一〇一 {2 —去氧一 3 —〇一 [(R) — 3 —甲氧癸基]—6 —〇一甲基一2— [(Ζ) -11—(十八碳烯醯胺基）]—4 —〇一膦酸基一β— D —吡喃葡糖基}一2，3—二一 ◦一十二基一α - D —毗喃葡糖基乙磺酸（以下稱爲化合物24 ) 2—(鱗酸基）乙基6 —〇一{2 —去氧一 3—〇一 [(R) 一 3—甲氧癸基]一 6—〇一甲基一 2— [(Ζ) —11—(十八碳烯醯胺基）]一 4一〇一膦酸基一 β— D —吡喃葡糖基}一2 -18 - 200413400 一〇——Η四基一 3—〇一癸基一α—D —吡喃葡糖苷（以下稱爲化合物2 5 )， 6—〇一{2一去氧—3 —〇一 [(R) — 3 —甲氧癸基]—6 一〇一甲基一 2 — [(Ζ) — 11—(十八碳烯醯胺基）]—4 一〇一膦酸基一β — D —吡喃葡糖基丨一1，3—二一〇一十二基一 β — D —吡喃葡糖基甲磺酸（以下稱爲化合物2 6 ) 2— （膦酸氧基）乙基6 —〇一{2—去氧一3 —〇一[(R )一 3—甲氧癸基；]一 2— [(Ζ) — 11一（十八碳烯醯胺基 )]一 4一〇一膦酸基一 β— D —吡喃葡糖基}一2，3 —二一〇一十二基一 α—D —吡喃葡糖苷（以下稱爲化合物27) -19 - 1 （膦酸氧基）乙基6 — ◦ — {2 —去氧一 3 —〇一 [(R )一 3—羥癸基]—2— [(Z) — 11—(十八碳烯醯胺基）] —4—〇一膦酸基—β — D —吡喃葡糖基}— 2，3—二一〇一十二基一 a— D —吡喃葡糖苷（以下稱爲化合物28)， 2—(膦酸氧基）乙基6 —〇一{2 —去氧一 3 —〇一 [(R )—3 —甲氧癸基]—6 —〇一甲基一 2— [(Z) —11—(十八碳烯醯胺基）]—4一〇一膦酸基—β一 D -吡喃葡糖基} —3 —〇一十二基一 2 —〇一[(3—氧基）十四基]—a— D —毗喃葡糖苷（以下稱爲化合物29 )， 2—(鱗酸氧基）乙基6—〇一{2 —去氧一 3 —〇一 [(R )—3 —甲氧癸基]—6 —〇一甲基—2 — [(Ζ) — 11—(十八碳烯醯胺基）]一 4 —〇一膦酸基一 β一 D -吡喃葡糖基} 200413400 一 2，3 —雙一〇一[(壬氧基）乙基]一 α— D —吡喃葡糖苷 (以下稱爲化合物30)，（膦酸氧基）乙基6 —〇一 {2 —去氧一 3一〇一 [(R )—3 —甲氧癸基]一 6 —〇一甲基一 2— [(Z) — 11— （十八碳烯醯胺基）]一 4一〇一膦酸基一 β— D —吡喃葡糖基} —2, 3—雙一〇一{2 — [2 —（己氧基）乙氧基]乙基} 一 α - D —吡喃葡糖苷（以下稱爲化合物3 1 )， 2—(膦酸氧基）乙基6 —〇一 {2 —去氧一 3 —〇一[(R )一 3 -甲氧癸基]—6 —〇一甲基一 2— [(Ζ) — 11—(十八碳烯醯胺基）]一 4一〇一膦酸基一 β— D —吡喃葡糖基} 一 2，3—雙一〇一 {2 — [2— (2—丙氧乙氧基）乙氧基] 乙基} — α — D —吡喃葡糖苷（以下稱爲化合物3 2 )， 2—（膦酸氧基）乙基6— 0 — {2 —去氧一 3 —〇一[(R )一 3 —甲氧癸基]一 6—〇一甲基一 2— [(Ζ) — 11—(十八碳烯醯胺基）]一 4 一 ◦一膦酸基—β — D — 口比喃葡糖基} —3 —〇一十二基一 2 —〇一[2—（十一碳磺醯基）乙基]— α — D —吡喃葡糖苷（以下稱爲化合物3 3 )， 2—(鱗酸氧基）乙基6 —〇一 {2 —去氧一 3 — ◦ — [(R )—3 —甲氧癸基]一 6 —〇一甲基一2 — [(Ζ) — 11—(十八碳烯醯胺基）]一 4一〇一膦酸基—β一 D —吡喃葡糖基} —2，3—雙一〇一 [2—（壬磺醯基）乙基]—α—D —吡喃葡糖苷（以下稱爲化合物34 )， 2— （膦酸氧基）乙基6-〇一 {2 —去氧一 3 —〇一 [(R )一 3—甲氧癸基]—6 —〇一甲基一 2 — [(Z) — 11— （十 -20 - 200413400 八碳烯醯胺基）]一 4 —3—〇一十二基—2 Q〜膦酸基一 β— D -毗喃葡糖基} 稱爲化合物3 5 0—[(3—氧基）十四烷醯基]—(X D —吡喃葡糖苷（以下膦酸基〇 {2〜去氧一3 —〇一[(R) — 3 —甲氧癸基]一 6 —〇一甲基一 )]—4 —〇一膦酸基 ' [(Ζ ) 一 11一（十八碳烯醯胺基四烷醯基]一 a- D —吡喃葡糖 D —吡喃葡糖基3—〇一十二基一2 —〇一 [(3 —氧基）十苷（以下稱爲化合物3 6 )或Mono (octadecenyl) amino group] -β-D-glucopyranosyl] -3 -◦ dodecyl-2-0-0 [(R)-3-hydroxytetradecyl] -a — D-glucopyranoside (hereinafter referred to as compound 4), phosphonate 3-0-decyl-6--0- [2-deoxy-4 10-phosphonic acid 3-〇-1 [(R ) — 3 —methoxydecyl] -6-〇-methyl-2 2 [(Z) -11 (eighteen 5 ^ fine brewing group) amino]-β-D-glucosyl]- 2-0-tetradecyl-a-D-U glucopyranosyl (hereinafter referred to as compound 5), -14-200413400 phosphonic acid group 3-0-decyl-6-0-[2-deoxy- 1 4-0-phosphonic acid group 3-10-[(R) -3-methoxydecyl] -6-〇-methyl-2 mono [(Z) -11- (octadecenyl) amine Group] -β-D-glucopyranosyl] -2-0-tetradecanyl-β-D-agrenoglucoside (hereinafter referred to as compound 6), phosphonic acid group 2,3-21010 Diyl-6-010- [2-deoxy-◦-phosphonic acid group 3 — ◦ — [(R) — 3-methoxydecyl] -6 〇-Methyl-2-[(Z) —11- (octadecylamino) amino] -β-D-P glucosyl] -a-D- glucosamine (hereinafter Called compound 7), phosphonic acid group 2,3-dioxalyl-12-yl-6-10-0- [2-deoxy-4-0-phosphonic acid group 3-0-[[R)-3- Methoxydecyl] -6-〇-methyl-2-[(Z) — 11- (octadecylchloroamido) amino] -β-D-glucopyranosyl] -β-D-pyridine Glucosinolate (hereinafter referred to as compound 8), phosphono group 2,3-dione ◦dodecyl-6-0— [2-deoxy-4—0-phosphono group—3--0 — [( R) —3-methoxydecyl] -6-O-methyl-2- [9- (octadecyl) amino] -β-D-II glucopyranosyl] -a-D-fluorene Glucosamine (hereinafter referred to as Compound 9) 'Phosphonic acid group 2,3-dione ◦dodecyl-6-0— [2—deoxy-4—0—phosphonic acid group 3—〇1 [(R) — 3-methoxydecyl] -6-O-methyl-2 2 [9- (octadecyl) amino] -β-D-glucopyranose 〕 -Β-D-glucopyranoside (hereinafter referred to as Compound 1 0), phosphono 2 '3-210-undecyl-6-0-[2-deoxy-4-15-200413400- ◦ Monophosphonic acid group 3—〇 — [(R) —3—methoxydecyl] to 6 to 0—methyl—2-[(E) — 9— (octadecenyl) amino] ~ Β ~ D -pyranoglucosyl] -α-D -glucopyranoside (hereinafter referred to as chemokine 11), phosphonic acid group 3-〇-decyl-6-〇-1 [2-deoxy ~ 4 ~ 〇 ~ Phosphinofluorenyl- 3-0-[(R) -3-methoxydecyl] -6--0-methyl-2 1 [(E) -9- (octadecenyl) Amine group]-β-D ~ glucopyranosyl]-2-◦-tetradecyl-β-D-glucopyranoside (hereinafter referred to as compound 12), phosphonic acid group 3-12 The group 6-〇- [2-deoxy-4-0-phosphonic acid group 3-0-[(R)-3-methoxydecyl] 6-〇-methyl-2 2 [(ζ) —11— (octadecenyl) amino] -β-D-glucopyranosyl] -2-0-tetradecyl-01-D-pyridine Glucoside (hereinafter referred to as compound 1 3), phosphonic acid group 3—12 dodecyl 6—0— [2 —deoxy-4 4—10—phosphonic acid group 3—0 — [(R) — 3 —Methoxydecyl] -6-methyl-1-2-[(Z) — 11- (octadecenyl) amino] -β-D-pyranoglucosyl] -2-0— Tetradecyl β-D-glucopyranoside (hereinafter referred to as Compound 1 4), 2- (phosphonooxy) ethyl 6-0 — [2—deoxy-4—◦monophosphonic acid group 3 —〇一 [(R) — 3-methoxydecyl] -6-〇-methyl-2 2-[(ζ) — 11- (octadecenyl) amino] -β-D-pyran Glucosyl]-3-12-dodecyl- 2-0-[(R)-3-hydroxytetradecyl]-α-D-glucopyranoside (hereinafter referred to as compound 15), -16- 200413400 2- (Linosinic acidoxy) ethyl 6-0- [2-deoxy-4-10-quanyl- 3-◦-[(R)-3 -methoxydecyl] -6-〇-1 Methyl- 2-[(Z)-11- (octadecenyl) amino]-β-D -glucopyranosyl]-3 〇 Dodecyl-2—0—tetradecyl—α—D—glucopyranoside (hereinafter referred to as compound 16), 2- (phosphonooxy) ethyl 6—〇— [2 —deoxy A 4-10 phosphonic acid group 3-0-[(R) —3-methoxydecyl] 6-〇-methyl-2 — [(Z) — 11- (octadecyl group) Amine group] -β-D-pyranoglucosyl] -2,3-21011 · yl-α-D-glucopyranosylglucoside (hereinafter referred to as compound 17), 2-a ( Phosphonic acidoxy) ethyl 6 1-[2 -deoxy-4 -10 -phosphonic acid -3 -0-[(R)-3 -methoxydecyl]-6 -0 -methyl-2 Mono-[(Z) — 11- (octadecylpyridinyl) amino] -β-D-glucopyranosyl] -2,3-1210-12yl-β-D-glucopyranosyl Glycoside (hereinafter referred to as Compound 1 8), 2-phosphonoethyl ethyl a- [2-deoxy-3-0-[(R) -3-methoxydecyl] -6-0-methyl-1 2-[(Z) —11- (octadecenyl) amino] -4,10-phosphonic acid-β-D-pyran Glycosyl] -2,3-dioxoyl-12-yl-a-D-glucopyranoside (hereinafter referred to as compound 1 9), 3- (phosphonooxy) propyl 6-10--2 Deoxy-3 10-[[R] -3 3-methoxydecyl] -6-〇-methyl-2 — [(Z) —11- (octadecenylamino)]-4—0 Monophosphonic acid group-β-D-glucopyranosyl group-2, 3-21012 dodecyl-a-D-glucopyranoside (hereinafter referred to as Chem-17-200413400 compound 2 0) , 3- (phosphono) propyl 6-0- {2-deoxy-3-0-[(R) -3-methoxydecyl] -ό-10-methyl-2 — [(Z) — 11- (octadecenylamino)] — 4— ◦ monophosphonic acid group β-D-glucopyranosyl group 丨 2, 3-12-120-dodecyl-α-D- Glucosinolate (hereinafter referred to as compound 2 1), 0-010- {2-deoxy-3—0-[(R) —3-methoxydecyl] -6—10-methyl-2 — [( (Z) — 11— (octadecylamino)] — 4—10—phosphonic acid group—β—D—pyranosyl group] —2, 3—dione—dodecyl—α-D —Pyridine Glucosyl methyl dihydrogen phosphate (hereinafter referred to as compound 22), 6-〇- {2-deoxy-3-0-[(R) -3-methoxydecyl] -6-010-methyl A 2-[(Z) — 11- (octadecenylamino)] 4 4 10-phosphonic acid group β-ϋ-glucopyranosyl group-2, 3-21010 Mono-α-D-glucopyranosylethyl dihydrogen phosphate (hereinafter referred to as compound 23), 6-010- {2-deoxy-3-0-[(R) -3-methoxydecyl ] -6-0-methyl-1 2-[(Z) -11- (octadecenylamino)]-4-0-phosphonic acid-β-D-glucopyranosyl} -2, 3-dioxyl-dodecyl-α-D-pyranoglucosylethanesulfonic acid (hereinafter referred to as compound 24) 2- (quanyl) ethyl 6-〇- {2-deoxy-1— 〇一 [(R) -3-methoxydecyl] -6-〇-methyl-1 2-[(Z) —11- (octadecenylamino)]-4-10 phosphonate- β- D -glucopyranosyl}-2 -18-200413400-10-tetrayl-3-0-decyl-α-D-glucopyranoside (hereinafter referred to as compound 2 5), 6- 〇- {2-deoxy-3—〇 — [(R) — 3-methoxydecyl] -6—10-methyl-2 — [(Z) — 11— (octadecenylamino) ] -4 10-phosphono-β-D-glucopyranosyl- 1,3-dioxoyl-β-D-glucopyranosyl methanesulfonic acid (hereinafter referred to as a compound 2 6) 2— (phosphonooxy) ethyl 6—〇— {2—deoxy—3—〇 — [(R) —3-methoxydecyl;] — 2 — [(Z) — 11— (Octadecenylamino)] 4-10 phosphono-β-D-glucopyranosyl} -2,3-dioxoyl-12-yl-D-glucopyranoside (Hereinafter referred to as compound 27) -19-1 (phosphonooxy) ethyl 6 — ◦ — {2 —deoxy-3—0 — [(R) —3-hydroxydecyl] —2— [(Z ) — 11 — (octadecenylamino)] — 4-0 monophosphonic acid group — β — D —glucopyranosyl group — 2-3,210-dodecyl-a-D — Gluconoside (hereinafter referred to as compound 28), 2- (phosphonooxy) ethyl 6—〇— {2 —deoxy—3—〇 — [(R) —3 —methoxydecyl] -6 —〇-methyl-2 — [(Z) — 11- (octadecenylamino)]-4-10 phosphono-β-D-glucopyranosyl} -3-0-dodecyl-2 2-〇-[(3-oxy ) Tetradecyl] —a—D—pyranoglucoside (hereinafter referred to as compound 29), 2- (quanyloxy) ethyl 6—0— {2 —deoxy—3—〇 — [(R) —3 —Methoxydecyl] -6—〇-methyl-2 — [(Z) — 11— (octadecenylamino)] — 4—〇—phosphonic acid group — β-D-pyran Glucosyl} 200413400 -2,3-bis-010-[(nonoxy) ethyl] -α-D-glucopyranoside (hereinafter referred to as compound 30), (phosphonooxy) ethyl 6- 〇一 {2-—Deoxy-3—010 — [(R) —3-methoxydecyl] —6-—O-methyl-2 — [(Z) — 11— (octadecenylamino) ] -1,4-10-phosphono-β-D-glucopyranosyl} -2, 3-bis-10 (1-[2- (hexyloxy) ethoxy] ethyl} -α- D-glucopyranoside (hereinafter referred to as compound 3 1), 2- (phosphonooxy) ethyl 6—〇— {2 —deoxy—3—〇 — [(R) —3-methoxydecyl ] -6-〇-methyl-1 2 — [(Z) — 11- (octadecenylamino)]-4,10-phosphonic acid-β-D-glucopyranosyl} -2,3-bis-10-1 {2 — [ 2- (2-propoxyethoxy) ethoxy] ethyl} — α — D —glucopyranoside (hereinafter referred to as compound 3 2), 2- (phosphonooxy) ethyl 6-0 — {2-Deoxy-3-O-[(R) -3-methoxydecyl] -6-O-methyl- 2-[(Z) — 11- (octadecenylamino)]- 4 mono-monophosphonic acid group-β-D-glucopyranosyl group} -3-0-12 dodecyl-2-0-[2-(undecylsulfonyl) ethyl]-α-D —Glucopyranoside (hereinafter referred to as compound 3 3), 2- (quanyloxy) ethyl 6—〇— {2 —deoxy—3 — ◦ — [(R) —3 —methoxydecyl] -6-O-methyl-2-[(Z)-11- (octadecenylamino)]-4-10-phosphono-β-D-glucopyranosyl} -2,3 —Bis-010- [2- (nonsulfonyl) ethyl] -α-D-glucopyranoside (hereinafter referred to as compound 34), 2- (phosphonooxy) ethyl 6-〇- {2 —Deoxy-3 〇一 [(R) -3-Methoxydecyl] -6-〇-methyl-1 2-[(Z) — 11- (ten-20-200413400 octaenylamino)]-4 3- 〇 Dodecyl-2 Q ~ phosphono-β-D-pyranoglucosyl} is called compound 3 5 0-[(3-oxy) tetradecanylamido]-(XD-glucopyranosyl Glycoside (following phosphonic acid group {{2 ~ deoxy-3-0-[(R) -3-methoxydecyl] -6-〇-methyl-1)] -4-0-phosphonic acid group '[( Z) -11- (octadecenylaminotetraalkylfluorenyl] -a-D-glucopyranosyl D-glucopyranosyl 3-00-dodecyl-2 2-〇-1 [(3 — Oxy) decaside (hereinafter referred to as compound 3 6) or

膦酸基6—〇一 {2〜去氧—3 —〇—[(R) 一3 —甲氧癸基]一 6 —〇一甲基一 2〜[(Z) 一 n一（十八碳烯醯胺基 )]一 4一〇一膦酸基〜β—D —吡喃葡糖基}_3 —〇—十二基一 2 —〇一 [(3 —氧基）十四烷醯基]—β— D 一吡喃蔔糖苷（以下稱爲化合物3 7 )。Phosphonic acid group 6—0— {2 ~ deoxy—3—0 — [(R) —3—methoxydecyl] —6—O—methyl—2 — [(Z) —n— (octadecyl Alkenylamino)] 4-410-phosphonic acid group ~ β-D-glucopyranosyl} _3--0-dodecyl-2-0-[[3-oxy) tetradecanyl] —Β- D-pyranoside (hereinafter referred to as compound 37).

再者’本發明爲有關含上述化合物（I )爲有效成分之醫藥’特爲’炎症之預防劑或治療劑，自體免疫疾病之預防劑或治療劑’免疫抑制劑，冠狀動脈旁路形成術後上預後改善劑，或敗血症預防劑或治療劑。上述式（I )中，Q及其中之順序無特定，例如，基-0-Aik-可爲- Ο-Alk-或- Alk-O-。上述式（I )中，Q中「Ci—Cs伸烷基」爲例如，亞甲基，伸乙基，伸丙基，三亞甲基等直鏈或分岐鏈C!— C 3伸烷基，宜爲亞甲基，伸乙基或三亞甲基，又宜爲伸乙基上述式（I )中，R3中「可有選自下述取代基群A之一 -21 - 200413400 種以上基取代之C 1 一 C 2 Q烷醯基」中「C 1 一 c 2 0烷醯基」，及取代基群A中「可有氧基之Cl — C2〇院醯氧基」中「Cl 一 C2G院醯基」部分爲例如，甲酸基（但有氧基取代基之場合除外），乙醯基，丙醯基，異丙醯基，丁醯基，異丁醯基，第二丁醯基，第三丁醯基，戊醯基，異戊醯基，特戊醯基，己醯基，異己醯基，庚醯基，異庚薩基，辛醯基，異辛醯基，壬醯基，異壬醯基，癸醯基，異癸醯基，-\—醯基，異Η ^醯基，十二醯基，異十二醯基，十三醯基，異十三醯基，十四醯基，十五醯基，十六薩基，十七醯基，十八碳嫌醯基，異十八碳燃醯基，十九醢基，二十醯基等直鏈或分岐鏈Ci - Cm院醯基，取代基群a中，宜爲C4 一 C!8院醯基’又宜爲Cs — Ci8焼醱基，又宜爲 C 1 0 — C 1 8火兀釀基’ R 且爲Ciq — Ci8院酸基。上述式（I )中，R3中「可有選自下述取代基群A之一種以上基取代之C3 - Cm烯醯基」中「c3—C2G烯醯基」’及取代基群A中「可有氧基之〇3 - C2Q嫌釀氧基」之「c3 — C2G烯醯基」部分爲上述Cl — C2〇烷醯基中C3 〜20’含1〜3個雙鍵之基’宜爲c4__ Cl8烯醯基，又宜爲Cio— (：18烯醯基。上述式（I )中’ R3中「可有選自下述取代基群A之一種以上基取代之C 3 — C 2〇炔醯基」中r C 3 — C 20炔醯基」’及’取代基群A中「可有氧基之c3 — C 20炔醯氧基」之〇3一炔醯基」部分，爲上述Cl 一 C 20烷醯基中 C3〜20者，其有個參鍵之者，宜爲c4— Cl8炔醯基 -22 - 200413400 ’又宜爲Cio — Cl8快釀基。上述式（I )中，Ri，R2及R4中「有選自如下述取代基群A之一種以上基取代之C ! 一 C 7 〇烷基i中「C 1〜rFurthermore, the present invention relates to a medicine containing the above-mentioned compound (I) as an active ingredient, and is particularly a preventive or therapeutic agent for inflammation, a preventive or therapeutic agent for autoimmune diseases, an immunosuppressive agent, and coronary artery bypass formation. Prognostic improvement agents, or preventive or therapeutic agents for sepsis. In the above formula (I), Q and the order thereof are not specific. For example, the group -0-Aik- may be -0-Alk- or -Alk-O-. In the above formula (I), "Ci-Cs alkylene" in Q is, for example, a straight or branched chain C! -C 3 alkylene such as methylene, ethylidene, propylidene, and trimethylene, Preferably it is methylene, ethylidene or trimethylene, and also ethylidene. In the above formula (I), "in R3, there may be one or more substituents selected from one of the following substituent groups A-21-200413400. "C 1 -C 2 Q alkyl" in "C 1 -c 2 0 alkyl" and "Cl-C 2G" The "institutional" part is, for example, formate (except when there are oxy substituents), ethylamido, propionyl, isopropylamyl, butylamyl, isobutylamyl, second butylamyl, third butylamyl, pentamidine Base, isopentyl, isopentyl, hexyl, isohexyl, heptyl, isoheptyl, octyl, isooctyl, nonyl, isononyl, decyl, isodecyl Base,-\ — fluorenyl, isofluorenyl, hexadecyl, hexadecyl, hexadecyl, hexadecyl, hexadecyl , Seventeen Carbonyl, Eighteen Carbon Base, isooctadecyl fluorenyl, nineteen fluorenyl, icosyl fluorenyl and other straight or branched chain Ci-Cm fluorenyl groups, in the substitution group a, should be C4-C! 8 linyl groups It should be Cs—Ci8 hydrazone, and also C 1 0—C 1 8 fire aryl group 'R and Ciq—Ci8 acid base. In the above formula (I), in R3, "the C3-Cm alkenyl group substituted with one or more groups selected from the following substituent group A" and "c3-C2G alkenyl group" in the substituent group A and " The "c3-C2G alkenyl group" which may have oxo-C2Q alkoxy group "is C3 ~ 20 'in the above-mentioned Cl-C20 alkyl group, which is preferably a group containing 1 to 3 double bonds. C4__Cl8 alkenyl, also preferably Cio — (: 18 alkenyl. In the above formula (I), “R3” may have C 3 —C 2 substituted with one or more groups selected from the following substituent group A. The "C 3 —C 20 alkynyl" group in the "alkynyl" group and the "03-alkynyl group" in the "c3-C20 alkynyloxy group that may have an oxygen group" in the substituent group A are the above Those of C3 ~ 20 in Cl-C20 alkyl group, and those having a bond, are preferably c4-Cl8 alkynyl-22-200413400 ', and also preferably Cio-Cl8 fast brewing group. In the above formula (I) In Ri, R2 and R4, "There is C! -C7oalkyl i substituted with one or more groups selected from the following substituent group A as follows:" C 1 ~ r

^ 2 C 院基」爲例如甲基，乙基，丙基，異丙基，丁基，異丁基，第二丁基，第三丁基，戊基，異戊基，2_甲基丁基，新戊基，1—乙基丙基，己基，異己基，4 -甲基戊基，3 -甲基戊基，2-甲基戊基，1-甲基戊基，3,3一二甲基丁基，2,2〜二甲基丁基，1，1 一二甲基丁基，1，2 —二甲基丁基，1，3〜一甲基丁基’ 2,3 — 一甲基丁基’ 2—乙基丁基，庚基，1 — 甲基己基，2—甲基己基，3 —甲基己基，4 一甲基己基，5 一甲基己基，1 一丙基丁基，4，4一二甲基戊基，辛基，i 一甲基庚基，2—甲基庚基，3—甲基庚基，4一甲基庚基， 5—甲基庚基，6—甲基庚基，1—丙基戊基，2—乙基己基，5，5—二甲基己基，壬基，3—甲基辛基，4 一甲基辛基，5—甲基辛基，6 一甲基辛基，i—丙基己基，2 一乙基庚基，6，6 —三甲基庚基，癸基，1 一甲基壬基，3 —甲基壬基，8—甲基壬基，3—乙基辛基，3，7—二甲基辛基，7， 7—二甲基辛基，十一基，4，8一二甲基壬基，十二基，十三基，十四基，十五基，3，7，11—三甲基十二基，十六基，4，8，12 —三甲基十三基，1 一甲基十五基，14 一甲基十五基，13，13 —二甲基十四基，十七基，15—甲基十六基，十八基，1一甲基十七基，十九基，二十基或3，7， 11’ 15 —四甲基十六基之ci-20直鏈或分岐鏈烷基，宜爲 C4 一 C18烷基，又宜爲c8 — CI8烷基。 -23 - 200413400 上述式（I )中，R1，R2及R4中「有選自如下述取代基群A之一種以上基取代之c 2— C 20烯基」中「C 2 - C 20 烯基」爲如上述C !一 C 20烷基中C2-C20者，含有1至3 個雙鍵之基，宜爲C1() 一 C18烯基。上述式（I )中，R1，R2及R4中「有選自如下述取代基群A之一種以上基取代之C 2 - C 2〇炔基」中「C 2〜C μ 炔基」爲如上述C : 一 C 2〇烷基中C2-C20者，含有1至3 個參鍵之基，宜爲ClG — Cl8快基。上述式（I )中，R5及取代基群A中「鹵原子」爲如氣，氯，溴或碘，宜爲氟，氯或溴，又宜爲氟。上述式（I )中，R5中「可有氧基之中「Ci— c6烷氧基」爲如甲氧基，乙氧基，丙氧基，異丙氧基，丁氧基，異丁氧基，第二丁氧基，第三丁氧基，戊氧基，異戊氧基，2—甲基丁氧基，新戊氧基，1 一乙_ 丙氧基，己氧基，異己氧基，4 一甲基戊氧基，3 —甲基戊氧基，2 —甲基戊氧基，1 一甲基戊氧基，3，3 —二甲基丁氧基，2，2 —二甲基丁氧基，1，1—二甲基丁氧基，1，2 一二甲基丁氧基，1，3—二甲基丁氧基，2，3—二甲基丁氧基或2 -乙基丁氧基之C1-C6直鏈或分岐鏈烷氧基，意爲CM-C4直鏈或分岐鏈烷氧基，又宜爲甲氧基。上述式（I )中，R5中「可有氧基之C2 — C6烯氧基」中「C2 — 06烯氧基」爲如上述烷氧基中，有2、6 個碳原子且含1個雙鍵之基，宜爲C2— C4烯氧基。上述式（I )中，R5中「可有氧基之C2 — C6炔氧基 -24 - 200413400 中「C2 — <36炔氧基」爲如上述Ci 一 C6院氧基中，有2-6 個碳原子且含1個參鍵之基，宜爲C 2 - C 4炔氧基。上述式（I )中，取代基群A中「可有氧基之CpCu 垸氧基」爲Cl-10直鏈或分岐鏈烷氧基（Cl — C2〇烷基）與氧原子結合之基，例如甲氧基，乙氧基，丙氧基，異丙氧基，丁氧基，異丁氧基，第二丁氧基，第三丁氧基，戊氧基，異戊氧基，2—甲基丁氧基，新戊氧基，1 一乙基丙氧基，己氧基，異己氧基，4 一甲基戊氧基，3 —甲基戊氧基’ 2—甲基戊氧基，1一甲基戊氧基，3，3一二甲基丁氧基，2，2 —二甲基丁氧基，1，1—二甲基丁氧基，1，2一二甲基丁氧基，1，3—二甲基丁氧基，2，3 —二甲基丁氧基，2 —乙基丁氧基，庚氧基，4 一甲基己氧基，丨一丙基丁氧基，4，4一二甲基戊氧基，辛氧基，6—甲基庚氧基，5 ’ 5—二甲基己氧基’壬氧基，癸氧基，1 一甲基壬氧基，3 一甲基壬氧基，8—甲基壬氧基，；3 —乙基辛氧基，3，7一二甲基辛氧基，7，7—二甲基辛氧基，十一氧基，4，8一 —•甲基壬興基’十_*與基，十三氧基，十四氧基，十五氧基，3，7，11 一三甲基十二氧基，十六氧基，4，8，12一三甲基十三氧基，1 一甲基十五氧基，14 一甲基十五氧基， 13，13—二甲基十四氧基，十七氧基，十八氧基，丨一甲基十七氧基，十九氧基，二十氧基或3，7，11，15 —四甲基十六氧基之C1-20直鏈或分岐鏈烷氧基。上述式（I )中，取代基群A中「（ C ! 一 C 2〇烷氧基） C ! 一 C 2〇烷氧基」爲如上述「c 1 一 C 20烷氧基」取代以1 -25 - 200413400 個如上述之「Ci — c2G烷氧基」，宜爲（Cl—C6烷氧基 )Cl 一 C6院氧基。上述式（I )中’取代基群A中「{ ( c 1 一 c 20烷氧基 )C 1 — C 20烷氧基丨c i 一 c 2〇烷氧基」爲如上述「（ C ! 一 C 2G院氧基）C 1〜C 20烷氧基」取代以1個如上述之「^ 2 C is based on, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, second butyl, third butyl, pentyl, isopentyl, 2-methylbutyl Group, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3- Dimethylbutyl, 2,2 ~ dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3 ~ monomethylbutyl '2,3 — Monomethylbutyl '2-ethylbutyl, heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-propyl Butyl, 4,4-dimethylpentyl, octyl, i-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl , 6-methylheptyl, 1-propylpentyl, 2-ethylhexyl, 5,5-dimethylhexyl, nonyl, 3-methyloctyl, 4-methyloctyl, 5-methyl Octyl, 6-methyloctyl, i-propylhexyl, 2-ethylheptyl, 6,6-trimethylheptyl, decyl, 1-methylnonyl, 3-methylnonyl , 8-methylnonyl, 3-ethyloctyl, 3,7-dimethyloctyl, 7,7-dimethyloctyl, undecyl, 4,8-dimethylnonyl, ten Diyl, tridecyl, tetradecyl, pentadecyl, 3,7,11-trimethyldodecyl, hexadecyl, 4,8,12-trimethyltridecyl, 1-methyldeca Pentayl, 14-methylpentadecyl, 13,13-dimethyltetradecyl, heptyl, 15-methylhexadecyl, octadecyl, 1-methylhexadecyl, 19-decyl, Eicosyl or 3,7,11'15-tetramethylhexadecyl ci-20 straight-chain or branched-chain alkyl, preferably C4-C18 alkyl, and also preferably c8-CI8 alkyl. -23-200413400 In the above formula (I), R1, R2 and R4 are "C 2-C 20 alkenyl groups" in "c 2-C 20 alkenyl groups substituted with one or more groups selected from the following substituent group A" "C2-C20 in the C! -C20 alkyl group as described above, a group containing 1 to 3 double bonds, preferably C1 ()-C18 alkenyl. In the above formula (I), R1, R2 and R4 in the "C 2 -C 2 alkynyl group substituted with one or more groups selected from the following substituent group A" are as follows The C2-C20 group in the above C: -C20 alkyl group, which contains 1 to 3 reference bonds, is preferably a ClG-Cl8 fast group. In the above formula (I), the "halogen atom" in R5 and the substituent group A is, for example, gas, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and more preferably fluorine. In the above formula (I), the "Ci-c6 alkoxy group" in R5 which may have an oxygen group is, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy Group, second butoxy group, third butoxy group, pentyloxy group, isopentyloxy group, 2-methylbutoxy group, neopentyloxy group, 1 ethyl-propoxy group, hexyloxy group, isohexyloxy group Methyl, 4-monomethylpentyloxy, 3-methylpentyloxy, 2-methylpentyloxy, 1 monomethylpentyloxy, 3,3-dimethylbutoxy, 2,2-di Methylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy or C1-C6 straight-chain or branched-chain alkoxy group of 2-ethylbutoxy group means CM-C4 straight-chain or branched-chain alkoxy group, and preferably methoxy group. In the above formula (I), the "C2-C6 alkenyloxy group which may have an oxygen group" in R5 is the "C2- 06 alkenyloxy group" in the above-mentioned alkoxy group, which has 2, 6 carbon atoms and contains 1 The base of the double bond is preferably C2-C4 alkenyloxy. In the above formula (I), "C2-C6 alkynyloxy which may have an oxygen group in R5-200413400" and "C2-< 36 alkynyloxy group" in R5 are as described in the above Ci-C6 alkoxy group. A group of 6 carbon atoms and 1 reference bond is preferably a C 2 -C 4 alkynyloxy group. In the above formula (I), the "CpCu alkoxy group which may have an oxygen group" in the substituent group A is a group in which a Cl-10 straight-chain or branched-chain alkoxy group (Cl-C20 alkyl group) is bound to an oxygen atom, For example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, second butoxy, third butoxy, pentoxy, isopentoxy, 2- Methylbutoxy, neopentyloxy, 1-ethylpropoxy, hexyloxy, isohexyloxy, 4-methylpentyloxy, 3-methylpentyloxy '2-methylpentyloxy 1,1-methylpentyloxy, 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy Oxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy, heptyloxy, 4-methylhexyloxy, monopropylbutyl Oxy, 4,4-dimethylpentyloxy, octyloxy, 6-methylheptyloxy, 5 '5-dimethylhexyloxy'nonyloxy, decyloxy, 1-methylnonyl Oxy, 3-methylnonyloxy, 8-methylnonyloxy, 3-ethyloctyloxy, 3,7-dimethyloctyloxy, 7,7- Dimethyloctyloxy, undecyloxy, 4,8-methyl nonhexyl'deca_ *, tridecyloxy, tetradecyloxy, pentadecyloxy, 3, 7, 11 Monotrimethyldodecyloxy, hexadecyloxy, 4,8,12 trimethyltridecyloxy, 1 monomethylpentadecyloxy, 14 monomethylpentadecyloxy, 13, 13— Dimethyltetradecyloxy, hexadecyloxy, octadecyloxy, monomethylhexadecyloxy, nonadecyloxy, icosyloxy or 3,7,11,15 -tetramethylhexadecyl C1-20 straight-chain or branched-chain alkoxy. In the above formula (I), the "(C! -C2Oalkoxy) C! -C2Oalkoxy" in the substituent group A is as described in the above-mentioned "c1-C20alkoxy" substituted with 1 -25-200413400 "Ci-c2G alkoxy groups" as mentioned above, preferably (Cl-C6 alkoxy) Cl-C6 alkyloxy. The "{(c 1 -c 20 alkoxy) C 1-C 20 alkoxy 丨 ci -c 2 alkoxy" in the 'Substituent Group A' in the above formula (I) is as described above "(C! C 2G alkoxy group) C 1 ~ C 20 alkoxy group "is replaced with one"

Cl—C2()院氧基」，宜爲{ (Ci—Cs烷氧基）Ci—Ce 院氧基} Cl — C6院氧基。上述式（1 )中’取代基群A中「可有氧基之C2—C2〇嫌氧基」爲上述「（：1〜（：2(3烷氧基」中，有2_6個碳原子且含1-3個雙鍵之基。上述式（I )中’取代基群A中「可有氧基之c2—C 20 炔氧基」爲上述「Cl〜c2G烷氧基」中，有2_6個碳原子且含1-3個参鍵之基。本發明中’氧基以燒基，烯基或炔基取代時，氧基不於 1位被取代。即，氧基被取代，烷基，烯基或炔基時各不含院醯基，烯醯基或炔醯基。上述式（I )中’取代基群A中「Cl—C 2〇烷磺醯基」爲上述C ! 一 c μ烷基結合以磺醯基，宜爲c ] 一 c 6烷磺醯基。上述式（I )中，取代基群A取代位置宜爲3位。上述式（I )中，Ri宜爲可有選自取代基群入取代基之 C 〜 4〜CU烷基或C4—C：!8烯基，又宜爲可有選自取代基群A取代基之c8— Cls烷基或c8〜c：ls烯基，更宜爲未取代或有選自取代基群A之羥基或氧基之取代基，c 10 — -26 - 200413400 C I8院基或C 10 - C l8燒基’特且爲未取代或有選自取代基群A之羥基或氧基之取代基，癸基，十二基，十四基，5 一十二碳烯基或7—十四碳烯基。上述式（I )中，R2宜爲可有選自取代基群A取代基之 C4— C1S院基或C4 一 Ci8儲基’又且爲可有邊自取代基群A取代基之C 10 - C 18院基或C 10 — C 18細基。上述式（I )中，R3宜爲可有選自取代基群A取代基之 Ci— C2G烷醯基，又宜爲可有選自取代基群A取代基之c 10 一 C i 8烷醯基。 _ 上述式（I )中，R4宜爲可有選自取代基群A取代基之 c4〜C18烷基或C4 一 C18烯基，又宜爲可有選自取代基群A取代基之C 10 - C 18院基或C 10 — C 18嫌基。上述式（I )中，R5宜爲幽原子，羥基或未取代Cl — c6烷氧基，又宜爲氟原子，羥基或甲氧基。上述式（I )化合物可形成鹽’此等鹽宜爲鈉鹽，鉀鹽 ’鎂鹽或鈣鹽等鹼金屬或鹼土金屬之鹽；三乙胺鹽，三甲胺鹽等有機鹼鹽。 · 本發明化合物（I )在大氣中放置，則有吸收水分，吸附水，成水合物之情形，此等水合物也包括在本發明之鹽〇再者，本發明化合物（I )可吸收其它溶劑，成溶劑合物之情形，此等溶劑合物也包括在本發明之鹽。上述式（I )化合物分子中可有不對稱碳原子，而存在各種S配位，R配位之立體異構物，此種個別異構物或其 -27 - 200413400 混合物也包括在本發明中。【實施方式】發明之實施最佳形態本發明一般式（I )化合物，可依以下方法，以已知化合物（II)爲原料而製造。"Cl-C2 () Hydroxy" is preferably {(Ci-Csalkoxy) Ci-CeHydoxy} Cl-C6Hydoxy. In the above formula (1), the "substituent group C2-C20 alkoxy group" in the 'substituent group A' is the aforementioned "(: 1 ~ (: 2 (3alkoxy)", which has 2 to 6 carbon atoms and A group containing 1-3 double bonds. Among the "substituent group C2-C20 alkynyloxy" in the substituent group A in the above formula (I) is 2-6 in the above-mentioned "Cl ~ c2G alkoxy" A group having 1 carbon atom and 1 to 3 reference bonds. In the present invention, when an 'oxy group is substituted with an alkyl group, an alkenyl group or an alkynyl group, the oxygen group is not substituted at the 1 position. That is, the oxygen group is substituted and the alkyl group is substituted. When alkenyl or alkynyl, each does not contain an ethylenyl, alkenyl or alkynyl group. The "Cl-C 2o alkylsulfonyl group" in the substituent group A in the above formula (I) is the above C! The c μ alkyl group is bonded with a sulfofluorenyl group, preferably c] -c 6 alkylsulfonylsulfonyl group. In the above formula (I), the substitution position of the substituent group A is preferably 3 positions. In the above formula (I), Ri is preferably There may be a C ~ 4 ~ CU alkyl group or C4-C:! 8 alkenyl group selected from a substituent group and a substituent group, and a c8-Cls alkyl group or c8 ~ group which may have a substituent group selected from the substituent group A c: ls alkenyl, more preferably unsubstituted or substituted with a hydroxyl group or an oxy group selected from the substituent group A , C 10 — -26-200413400 C I8 courtyard group or C 10-C 18 alkyl group is particularly unsubstituted or substituted with a hydroxyl group or an oxy group selected from the substituent group A, decyl, dodecyl, Tetradecyl, 5 dodecenyl or 7-tetradecenyl. In the above formula (I), R2 is preferably C4-C1S or C4-Ci8 which may have a substituent selected from the substituent group A. C 'is a C 10-C 18 radical or a C 10-C 18 fine radical which may have a substituent from the side of the substituent group A. In the above formula (I), R3 may be optionally selected from the group of substituents. The Ci—C2G alkylfluorenyl group of the A substituent may also be a c 10 -C i 8 alkylsulfanyl group that may be selected from the substituent group A. In the above formula (I), R4 may be optionally selected from The C4-C18 alkyl group or C4-C18 alkenyl group of the substituent group A of the substituent group A is preferably a C10-C18 alkyl group or a C10-C18 alkyl group which may be selected from the substituent group A of the substituent group. In the formula (I), R5 is preferably a ply atom, a hydroxyl group or an unsubstituted Cl-c6 alkoxy group, and is also preferably a fluorine atom, a hydroxyl group or a methoxy group. The compound of the above formula (I) can form a salt, and these salts are preferably Sodium, potassium, 'magnesium or calcium salts' alkali metals or alkaline earth Salts of metal; organic base salts such as triethylamine salt, trimethylamine salt, etc. · When the compound (I) of the present invention is left in the air, it may absorb water, adsorb water, and form hydrates. These hydrates are also included in Salts of the present invention. Furthermore, when the compound (I) of the present invention can absorb other solvents and form solvates, these solvates are also included in the salts of the present invention. The compounds of the above formula (I) may or may not contain Carbon atoms are symmetrical, and various S-coordination and R-coordination stereoisomers exist. Such individual isomers or mixtures thereof -27-200413400 are also included in the present invention. [Embodiment] Best Mode for Carrying Out the Invention The compound of the general formula (I) of the present invention can be produced by using a known compound (II) as a raw material according to the following method.

(II)(II)

Aa1Aa1

(IX)(IX)

-28 - 200413400-28-200413400

RR

10'10 '

Ba1 NHCOCF3Ba1 NHCOCF3

〇R4a (XVI) 〇H (XV)〇R4a (XVI) 〇H (XV)

OHOH

R 10、R 10,

.·〇 nhc〇2ch2cci3. · 〇 nhc〇2ch2cci3

Ba3 H〇、、'、Ba3 H〇 ,, ',

nhc〇2ch2cci3nhc〇2ch2cci3

Ba4 ·.〇 OR 5a H〇、、Ba4 ..〇 OR 5a H〇 ,,

nhc〇2ch2cci3 〇R4a (XVII) ,nOR11 〇R4a (XVIII)nhc〇2ch2cci3 〇R4a (XVII), nOR11 〇R4a (XVIII)

Ba5 (r12o)2(〇)p〇、、、’Ba5 (r12o) 2 (〇) p〇、、、 ’

Ba6 OR4a (XIX) "NHCOsCHsCCIa 〇R4a (XX) OR ,〇、/〇H (R12〇)2(〇)P〇、Ba6 OR4a (XIX) " NHCOsCHsCCIa 〇R4a (XX) OR, 〇, / 〇H (R12〇) 2 (〇) P〇,

NHCO2CH2CCI3NHCO2CH2CCI3

Ba7 (r12〇)2(〇)p〇、'、’Ba7 (r12〇) 2 (〇) p〇, ','

,〇、/〇C(NH)CCI3 nhc〇2ch2cci3, 〇、 / 〇C (NH) CCI3 nhc〇2ch2cci3

〇R4a (XXI) 〇R4a (XXII) -29 - 200413400〇R4a (XXI) 〇R4a (XXII) -29-200413400

nhc〇2ch2cci3 H〇、、'、nhc〇2ch2cci3 H〇 ,, ',

Bb1 〇R (XVIII) OSiR13R14R15Bb1 〇R (XVIII) OSiR13R14R15

k、〇R 11 OSiR13R14R15k, 〇R 11 OSiR13R14R15

nhc〇2ch2cci3 k、〇Rnhc〇2ch2cci3 k, 〇R

Bb2 11Bb2 11

Bb4 (R120)2(〇)P〇N〇，^r ，/，/NHC02CH2CCI3 (R120)2(0)P0s0, ^NHCOsC^CCIs OR (XXIV) 〇R4a (XXV)Bb4 (R120) 2 (〇) P0N〇, ^ r, /, / NHC02CH2CCI3 (R120) 2 (0) P0s0, ^ NHCOsC ^ CCIs OR (XXIV) 〇R4a (XXV)

、、〇R 11, 〇R 11

Bb5Bb5

.〇、JDH.〇, JDH

Bb6 (r12〇)2(〇)p〇、、° ^^、nhc〇2ch2cci3 (r12〇)2(〇)p〇、'、* \ /、nhc〇2ch2cci3Bb6 (r12〇) 2 (〇) p0, ° ^^, nhc〇2ch2cci3 (r12〇) 2 (〇) p0, ', * \ /, nhc〇2ch2cci3

〇R4a (XXVI) 〇R (XXVII)〇R4a (XXVI) 〇R (XXVII)

OC(NH)CCI3 (R120)2(〇)P〇nX'' ^NHCOsCHsCCIs 0R4a (XXVIII) OHOC (NH) CCI3 (R120) 2 (〇) P〇nX '' ^ NHCOsCHsCCIs 0R4a (XXVIII) OH

k、〇R 11k, 〇R 11

Bc1 (r12〇)2(〇)P〇、、°. 丫、HC〇2CH2CCl3 (R12〇)2(〇)P〇、〇R4a (XXV)Bc1 (r12〇) 2 (〇) P〇 ,, °. Ya, HC〇2CH2CCl3 (R12〇) 2 (〇) P〇, 〇R4a (XXV)

k、〇R 11 nhc〇2ch2cci3 〇r43 (XXIX)k, 〇R 11 nhc〇2ch2cci3 〇r43 (XXIX)

Bc2 (r12〇)2(〇)p〇、Bc2 (r12〇) 2 (〇) p〇,

Bc3 nhc〇2ch2cci3 (r12〇)2(〇)p〇、vBc3 nhc〇2ch2cci3 (r12〇) 2 (〇) p〇, v

OC(NH)CCI3 nhc〇2ch2cci3OC (NH) CCI3 nhc〇2ch2cci3

OR (XXX) 0R4a (XXXI) -30 - 200413400OR (XXX) 0R4a (XXXI) -30-200413400

Bd2 nhc〇2ch2cci3 (XXXV) (XIX) nhco2ch2cci3 f (XXXVI) Bdw 〇R4aBd2 nhc〇2ch2cci3 (XXXV) (XIX) nhco2ch2cci3 f (XXXVI) Bdw 〇R4a

Bd4Bd4

nhc〇2ch2cci3 (XXII!)nhc〇2ch2cci3 (XXII!)

-31 - 200413400-31-200413400

OC(NH)CCI3 nhc〇2ch2cci3 〇R4a Η〇·OC (NH) CCI3 nhc〇2ch2cci3 〇R4a Η〇 ·

Ca1 r7〇、、'Ca1 r7〇 ,, '

(XXII)(XXVIII)(XXXI)(XXII) (XXVIII) (XXXI)

X wOR1(XI) (r12〇)2(〇)p〇vX wOR1 (XI) (r12〇) 2 (〇) p〇v

(XXXVII)(XXXVII)

Ca2 nhc〇2ch2cci3 r7〇〆 OR 4a (r12〇)2(〇)p〇、、、’Ca2 nhc〇2ch2cci3 r7〇〆 OR 4a (r12〇) 2 (〇) p〇、、、 ’

Ca3 〇R4a .〇、一〇H (r12〇)2(〇)p〇、、' (h〇)2(〇)p〇、、、’Ca3 〇R4a .〇, 10H (r12〇) 2 (〇) p0, '(h〇) 2 (〇) p〇 ,,'

、〇R1 (XL) •〇、^〇p(〇)(〇h)2 〇R4a "OR1 VOR10r2 (XXXVIII), 〇R1 (XL) • 〇, ^ 〇p (〇) (〇h) 2 〇R4a " OR1 VOR10r2 (XXXVIII)

Ca4 (R12〇)2(0)P〇、、、’ NHCOR3a R70、、° \ ’ 〜"〇R1 〇r2 (XXXIX) 〇p(〇)(〇R8)2 Ca5 (XL I) -32 - 200413400 R5Ca4 (R12〇) 2 (0) P〇 ,,, 'NHCOR3a R70 ,, ° \' ~ " 〇R1 〇r2 (XXXIX) 〇p (〇) (〇R8) 2 Ca5 (XL I) -32- 200413400 R5

OC(NH)CCI3 (R12〇)2(〇)P〇、'、' Y^#//NHC〇2CH2CCI3 HO'、' OR4a R5OC (NH) CCI3 (R12〇) 2 (〇) P〇, ',' Y ^ # // NHC〇2CH2CCI3 HO ',' OR4a R5

(XXII)(XXVIII)(XXXI) HO*(XXII) (XXVIII) (XXXI) HO *

op(〇)(〇r8)2 ’Or1 —咖 (XIV) (r12〇)2(〇)p〇、、°· "nhc〇2ch2cci3 h〇、、" OR4a R5op (〇) (〇r8) 2 ’Or1 —Ka (XIV) (r12〇) 2 (〇) p〇 ,, " nhc〇2ch2cci3 h〇, " OR4a R5

op(〇)(〇r8)2 、〇R1 ——^or2 (XL11)op (〇) (〇r8) 2, 〇R1 —— ^ or2 (XL11)

、〇p(〇)(〇r8)2(R12〇)2(0)P〇、wlxY^、NHCOR3a HO、、，、 Cb3Rs 0R4a 0R2 (XLIM)〇p (〇) (〇r8) 2 (R12〇) 2 (0) P〇, wlxY ^, NHCOR3a HO ,,,, Cb3Rs 0R4a 0R2 (XLIM)

、〇p(〇)(oh)2 (H〇)2(〇)p〇'、' ^y^、NHC〇R3a h〇、'、' (XL IV) R5〇p (〇) (oh) 2 (H〇) 2 (〇) p〇 ',' ^ y ^, NHC〇R3a h〇, ',' (XL IV) R5

^X^Ss0P(0)(0R8)2 (R120)2(0)Pax〇'V^*，///NHC0R3a Cb4 OR2 "OR4b (XUIIa) R 4c’ R5^ X ^ Ss0P (0) (0R8) 2 (R120) 2 (0) Pax〇'V ^ *, // NHC0R3a Cb4 OR2 " OR4b (XUIIa) R 4c ’R5

J"^^0P(0)(0R8)2 (Π120)2(0)ΡαΝ〇Λγ^^ΝΗ00Ρ39 ΗσΝ°\^^〇ρΐ Q OR2 (XLIilb)J " ^^ 0P (0) (0R8) 2 (Π120) 2 (0) ΡαΝ〇Λγ ^^ NΗ00Ρ39 ΗσΝ ° \ ^^ 〇ρΐ Q OR2 (XLIilb)

R -33 - 4(/ 200413400R -33-4 (/ 200413400

-34 - 200413400 R5-34-200413400 R5

°"^^P{0)(OR&)2° " ^^ P (0) (OR &) 2

(h〇)2(〇)p〇、(h〇) 2 (〇) p〇,

、NHC〇R3a H〇、、、’, NHC〇R3a H〇 ,,, '

.’"OR1. ’&Quot; OR1

-35 - 200413400-35-200413400

Eb3Eb3

-36 - 200413400 R5-36-200413400 R5

，〇C(NH)CCI3 >rrr，"V0P(0)(0R8)2 +, 〇C (NH) CCI3 > rrr, " V0P (0) (0R8) 2+

Fb1 (R120)2(0)P0sN° ，,//nhco2ch2cci3 HOx〇 //yOR1Fb1 (R120) 2 (0) P0sN °, // nhco2ch2cci3 HOx〇 // yOR1

OR 4aOR 4a

(XXII)(XXVIII)(XXXI) 〇r2 (LX IX)(XXII) (XXVIII) (XXXI) 〇r2 (LX IX)

OP(0)(OR8)2OP (0) (OR8) 2

Fb2 (R12〇)2(〇)P〇、、° 'NHC02CH2CCI3 ΗΟνΝ〇 #//OR1〇R4a or2 (LXX) R5 ,〇、>〇- 、〇p(〇)(〇r8)2 (R120)2(0)P0x〇' W/NHCOR3a HO、、'' W/〇R1 OR4a OR2 R5 〆〇、>〇Fb2 (R12〇) 2 (〇) P〇, ° 'NHC02CH2CCI3 ΗΟνΝ〇 # // OR1〇R4a or2 (LXX) R5, 〇, > 〇-, 〇 (〇) (〇r8) 2 (R120) 2 (0) P0x〇 'W / NHCOR3a HO, `` W / 〇R1 OR4a OR2 R5 〆〇, > 〇

Fb3 (H〇)2(〇)P〇、''、、Y^、NHC〇R3a H〇、、°Fb3 (H〇) 2 (〇) P〇, '' ,, Y ^, NHC〇R3a H〇 ,, °

(LXX I) •〇p(〇)(oh)2(LXX11)(LXX I) 〇p (〇) (oh) 2 (LXX11)

-37 - 200413400-37-200413400

丫〇\/\/〇P(〇)(〇R8)2 H〇、°’.^Y^'OR1 —~ or2 (LXXVII)〇〇 \ / \ / 〇P (〇) (〇R8) 2 H〇, ° ’. ^ Y ^ 'OR1 — ~ or2 (LXXVII)

OR4a (r12〇)2(〇)p〇、''、OR4a (r12〇) 2 (〇) p〇, ``,

NHC〇R3a (h〇)2(〇)p〇、、NHC〇R3a (h〇) 2 (〇) p〇 ,,

〇r2 (LXXVII I)〇r2 (LXXVII I)

OP(〇)(〇R8)2 (XII la) OHOP (〇) (〇R8) 2 (XII la) OH

上述工程中，R1，R2，R4及R5之定義如上。 R 3a爲可有選自如下取代基群之一種以上基取代之C ! 一 Ci9院基，C2— Cl9烯基或C2— Ci9炔基，該取代基群爲鹵原子，羥基，氧基，可有氧基之Ci-C 2〇院氧基，可有氧基之C2 — C2O烯氧基，可有氧基之C2 —C20快氧基，可有氧基之Cl 一 C20院釀氧基’可有氧基之C3 - C 20烯醯氧基及可有氧基之C3 - C 20炔醯氧基。 -38 - 2〇〇4l34〇〇只〇爲如上述R4之定義，但不包含氫原子。 R4b爲羥基保護基，宜爲4 一甲氧苄氧基。 R 4e爲可有選自如上取代基群A之一種以上基取代之C ! —C ! 7烷基，可有選自如上取代基群A之一種以上基取代之（：2— 烯基或可有選自如上取代基群A之一種以上基取代之C2— C17炔基，宜爲Ci — C15烷基或Ci — (：15烯基，又宜爲Cl — Ci5院基。 R5a爲經基保護基，宜爲苄氧鑛基或燒丙氧鑛基。In the above project, R1, R2, R4 and R5 are defined as above. R 3a is C which may be substituted with one or more groups selected from the following substituent groups: a Ci9 group, a C2-Cl9 alkenyl group or a C2-Ci9 alkynyl group, and the substituent group is a halogen atom, a hydroxyl group, an oxy group, or Ci-C 2o oxygen with oxygen, C2-C2O alkenyloxy with oxygen, C2-C20 fast oxygen with oxygen, Cl-C20 oxygen with oxygen '' C3-C20 alkenyloxy which may be oxy and C3-C20 alkynyloxy which may be oxy. -38-2004l34 00 is defined as R4 above, but does not include a hydrogen atom. R4b is a hydroxy-protecting group, preferably 4-monomethoxybenzyloxy. R 4e is a C! -C! 7 alkyl group which may be substituted by one or more groups selected from the above-mentioned substituent group A, and may be substituted by one or more groups (: 2-alkenyl or may be selected from the above-mentioned substituent group A) A C2-C17 alkynyl group substituted by one or more groups selected from the above-mentioned substituent group A, is preferably Ci-C15 alkyl or Ci-(: 15 alkenyl, and also preferably Cl-Ci5 alkyl group. R5a is protected by a radical The base is preferably benzyl or oxypropion.

R5b爲可有氧基之Cl 一 c6烷基。 R5e爲氫原子或鹵原子。 R6爲三（C!—C6烷基）矽基， R 7爲烯丙氧羰基， R8及R12爲相同或不同，各爲烯丙基，可有取代基之C 6— C1G芳基或可有取代基之C7 — Cn芳烷基，宜爲烯丙基，苯基或苄基。R5b is Cl-c6 alkyl which may have oxygen. R5e is a hydrogen atom or a halogen atom. R6 is a tri (C! -C6 alkyl) silyl group, R7 is an allyloxycarbonyl group, R8 and R12 are the same or different, each is an allyl group, and a C6-C1G aryl group which may have a substituent or may The C7-Cn aralkyl group as a substituent is preferably allyl, phenyl or benzyl.

R9及R1G爲相同或不同，各爲氫原子，Cf C6烷基或 C 6 - c 1 0 芳基。 R11爲1 一丙條基。 R13，R14及R15爲相同或不同，各爲CpC*烷基或C 6 - C i 〇芳基。 R16爲Ci — C6院基。 R17爲Ci一 C6院基。本發明化合物（Ϊ )之製造工程如下A〜η法。 (1) Α法爲製造中間體（XI) ，（XIa)或（χιν)之 -39 - 200413400 方法。 (2 ) B法爲製造中間體（XXII) ，（XXVIII)及（ XXXI )之工程。依R 5種類，各記載a法，b法及c法之 3種方法。 (3 ) C法爲令中間體（XI) ，（ XIa)或（XIV)與中間體（XXII) ，（ XXVIII)或（XXXI)縮合，而製造目的化合物（XLI) ，（ XLIV)或（XXXIX)之工程。 (4) D法爲製造中間體（XLVII)，與中間體（χχπ) ，（XXVIII)或（XXXI)縮合，而製造目的化合物（l) 之工程。 (5) Ε法爲製造Q爲伸乙氧基之目的化合物（Lxn)的工程。 (6) F法爲製造Q爲亞甲基之目的化合物（LXXII)的工程。 (7) G法爲製造Q爲三亞甲二氧基之目的化合物（ LXXVIII )的工程。 (8) Η法爲製造R1爲癸基之中間體（xiVa)的工程。以下，爲各工程之説明。 (1 ) A 法 (第A a 1工程）本工程爲令一丙酮一 D -葡萄糖化合物（π)之3位經基予以烷基化（包含導入烯基，炔基之場合。以下，製造工程説明中’有相同之定義。）或製造醯基化之化合物（ III)之工程，烷基化以下述（a)方法，醯基化以下述（b)方法 -40 - 200413400 來達成。 (a) 烷基化本工程爲於惰性溶劑中，於鹼存在下，令化合物（II ) 與烷化劑反應而達成。所使用溶劑爲例如，二噚烷，四氫呋喃等醚類；甲醯胺，二甲基甲醯胺等醯胺類；二氯甲烷等鹵化烴類，宜爲二甲基甲醯胺。所使用鹼爲例如，氫氧化鈉，氫氧化鉀等鹼金屬氫氧化物；正丁鋰，第三丁鋰等烷鋰類；氫化鉀，氫化鈉等鹼金屬氫化物等，宜爲氫化鈉。所使用烷化劑爲例如，鹵化烴類，磺酸酯類，宜爲溴化物（R 2 B r )或甲磺酸酯（R 2〇S〇2M e )。反應温度通常爲〇°C〜100°C下進行，宜爲0°C〜60°C。 '反應時間可視反應温度，原料，試劑或所使用溶劑等而異，通常，20分〜48小時，宜爲2〜24小時。反應終了後，本反應目的化合物可依常法，自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (b) 醯基化本工程爲於惰性溶劑中，於縮合劑及鹼存在或不存在下 ’令化合物（II )與羧酸或酸鹽化物等醯化劑反應而達成 -41 - 200413400 所使用溶劑爲例如，四氫呋喃，二曙烷等醚類；二氯甲烷，氯仿，四氯化碳等鹵化烴類；n，n—二甲基甲醯胺等醯胺類，宜爲二氯甲烷。羧酸反應所使用縮合劑爲1，3-二環己基碳化二亞胺，1，3-二異丙基碳化二亞胺，1-[3-(二甲胺基）丙基卜3-乙基碳化二亞胺氫氯（WSCI)等碳化二亞胺類，宜爲1，3-二環己基碳化二亞胺。酸鹽化物反應所使用鹼爲毗啶，二甲胺吡啶，三乙胺等 φ 有機鹽基類，宜爲4-二甲胺吡啶。所使用醯化劑爲式：R2’〇H之羧酸，或式：R2’C 1 ( 式中，R2'爲R2定義中院酿基，嫌醯基或炔醯基。）所表醯氯。此醯化劑含有羥基或氧基時，此基亦可被保護，例如，令氧基以縮醛基被保護。反應温度通常爲0°C〜l〇〇°C，宜爲15°C〜25°C (室温）〇反應時間通常爲20分〜24小時，宜爲1〜5小時。 # 反應終了後，本反應目的化合物可依常法，自反應混合物收集。例如，將反應混合物過濾，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A a 2工程） -42 - 200413400 本工程爲將化合物（III)，於烯丙醇溶劑中，在鹽酸氣之存在下加熱而得化合物（IV )之工程。反應温度通常爲0°c〜溶劑加熱回流温度下進行，宜爲室温〜80°c。反應時間通常爲20分〜24小時，宜爲1〜5小時。 (第A a 3工程）本工程爲在化合物（IV )之4位及6位羥基架以亞異丙基，而得化合物（V )之工程。本工程可令化合物（IV ) ，於惰性溶劑中，在酸觸媒存在下，與2，2 —二甲氧丙烷反應而達成。所使用溶劑爲例如，二甲基甲醯胺等醯胺類。所使用酸觸媒爲對-甲苯磺酸，莰磺酸等。反應温度通常爲室温〜5 0 °C。反應時間通常爲2 0分〜2 4小時。反應終了後，本反應目的化合物（V )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A a 4工程）本工程爲令化合物（V )之2位羥基烷化，而得化合物（ VI)之工程，可依第A a 1工程之反應而達成。 (第A a 5工程） -43 - 200413400 本工程爲令架在化合物（VI ) 4位及6位羥基之亞異丙基予以脫保護，而製造化合物（V Π )之工程。本工程爲令化合物（VI )，於醇溶劑中，與酸觸媒或N B S反應而達成。所使用溶劑爲例如，甲醇，乙醇等醇類。所使用酸觸媒爲對一甲苯磺酸，莰磺酸等有機酸；鹽酸，硫酸等無機酸。反應温度通常爲〇 °c〜5 0 °C，宜爲室温。反應日寸間通吊爲6分〜24小時，宜爲30分。反應終了後，本反應目的化合物（VII)可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A a 6工程）本工程爲令化合物（VII)烯丙基之雙鍵移爲烯醇醚型， · 以製造化合物（VIII)之工程。本工程可令化合物（vii) ，於惰性溶劑中，與鹼或銥錯合物反應而達成。所使用溶劑爲例如，四氫呋喃，二噚烷等醚類；二甲亞颯等亞颯類，當使用鹼時，宜爲二甲亞礪，當使用銥錯合物時，宜爲四氫呋喃。所使用驗爲例如，第三丁氧化鉀，甲氧化鈉，乙氧化鈉等鹼金屬烷氧化物，宜爲第三丁氧化鉀。 -44 - 200413400 所使用銥錯合物爲例如，（1，5 -環辛基二烯基）雙（甲二苯膦）銥（I )六氟磷酸鹽。反應温度當使用驗時，通常爲室温〜溶劑加熱回流温度，當使用銥錯合物時，通常爲〜8〇。(：，宜爲室温。反應時間當使用鹼時，通常爲1小時〜24小時，宜爲1 小時。反應終了後，本反應目的化合物（VIII )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A a 7工程）本工程爲將化合物（VIII )之二醇之一級羥基以矽烷基保護，而製造化合物（IX )之工程。本工程爲令化合物（ VIII )，於惰性溶劑下，在鹼存在下，與矽烷化劑反應而達成。所使用溶劑爲例如，四氫呋喃，二曙烷等醚類；二氯甲烷，氯仿，四氯化碳等鹵化烴類，宜爲二氯甲烷或四氫呋喃。所使用鹼爲例如，吡啶，二甲胺吡啶，三乙胺等有機鹽基類。所使用矽烷化劑爲，例如，氯化第三丁二甲砂院基等齒化三院砂院基。 200413400 反應温度通常爲〇°C〜80°C，宜爲室温。反應時間通常爲6分〜24小時。反應終了後，本反應目的化合物（IX )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層’以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A a 8工程）本工程爲令化合物（IX )之二級羥基以矽烷基保護，而製造化合物（X )之工程。本工程可令化合物（IX )，於惰性溶劑下，在鹼存在下，與醯化劑，再與醇類反應而達成。所使用溶劑爲例如，四氫呋喃，二噚烷等醚類；苯，甲苯，二甲苯等芳香族烴類；二氯甲烷，氯仿，四氯化碳，二氯乙烷，氯苯等鹵化烴類。所使用鹼爲例如，吡啶，二甲胺吡啶，三乙胺等有機鹽基類。所使用醯化劑爲。所使用醇類爲烯丙醇。反應温度通常爲一20°C〜50°C，宜爲〇°C。反應時間在加入醯化劑後而加入醇類前，通常爲1 0分〜 1小時，宜爲1 〇分，加入醇類後，反應時間通常爲1 0分〜1小時，宜爲1小時。 -46 - 200413400 反應終了後，本反應目的化合物（x)可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層 ’以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A a 9工程）本工程爲令化合物（X )之矽烷保護基予以脫保護，而製造一級醇之化合物（XI )之工程。本工程可令化合物（X φ )，於惰性溶劑下，與酸觸媒反應而達成。所使用溶劑爲例如，四氫呋喃，二曙烷等醚類；乙腈等腈類；二氯甲烷，氯仿，四氯化碳，二氯乙烷，氯苯等鹵化烴類。所使用酸觸媒爲例如，鹽酸，氫氟酸等無機酸；對甲苯磺酸等有機酸。反應温度通常爲20°C〜50°C，宜爲室温。反應時間通常爲6分〜2小時，宜爲1 5分。籲反應終了後，本反應目的化合物（XI )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (弟A a 10工程） -47 - 200413400 本工程爲令化合物（x)之矽烷保護基予以脫保護，再令正位異構化之烯醇醚同時脫保護，而製造一級醇化合物（ XIa )之工程。本工程可依第A a 9工程較嚴苛之反應條件，例如較長反應時間而達成。反應時間通常爲4小時〜24小時，宜爲1 〇小時〜1 6小時。反應終了後，本反應目的化合物（XIa )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A b 1工程）本工程爲令化合物（VI)烯丙基雙鍵予氧化切斷得醛後，還原，而製造化合物（XII)而工程。本工程爲令化合物 (VI )，於惰性溶劑下，與氧化劑反應，再於惰性溶劑下，與還原劑反應而達成。氧化反應所使用溶劑爲例如，四氫呋喃，二噚烷等醚類與水之混合溶劑，還原反應所使用溶劑爲例如，甲醇，乙醇等醇類。所使用氧化劑爲例如，四氧化鎢及過碘酸鈉之組合。所使用還原劑爲例如，氫化鋰鋁，硼氫化鈉等金屬氫化物類，宜爲硼氫化鈉。反應温度通常爲0 °C〜5 0 °c，宜爲室温。 -48 - 200413400 反應時間通常爲6分〜24小時。反應終了後，本反應目的化合物（XII )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第A b 2工程）本工程爲令化合物（XII)變換爲亞磷酸酯，又氧化，而鲁製造化合物（XIII )之工程。本工程可令化合物（XII )，於惰性溶劑下，在弱酸1H-四唑存在下，與胺基磷酸二異丙酯反應’再於惰性溶劑下，與氧化劑反應而達成。所使用溶劑爲例如，四氫呋喃，二噚烷等醚類；二氯甲烷，氯仿，四氯化碳，二氯乙烷，氯苯等鹵化烴類。所使用氧化劑爲例如，過氧化氫，間氯過苯甲酸，oxone 等過氧化物。反應温度通常爲0°C〜100 °C，宜爲室温。 _ 反應時間通常爲6分〜24小時。反應終了後’本反應目的化合物（XIII )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層’以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，砂膠層析等精製。 -49 - U4134〇〇 (第A b 3工程）本工程爲令化合物（ΧΠΙ)中4位及6位羥基架橋之亞裹丙基予以脫保護，而製造化合物（XIV)之工程，可依第A a 5工程之條件進行反應而達成。 (第A c 1工程）本工程爲令已知化合物（LI )之4位及6位羥基架以亞異丙基，再令1位羥基予以烯丙基化，而得化合物（Via ) 之工程，亞異丙基架橋工程可依第A a 3工程之條件進行反應而達成，烯丙基化工程可依第A a 1工程中烯丙基化之條件進行反應而達成。 (第A c 2工程）本工程爲令化合物（Via) 2個羥基予烷化，而得化合物 (VIb )之工程，可仿第A a 1工程之條件進行反應而達成〇 (第A c 3工程）本工程爲令已知化合物（LII )之4個乙醯基除去，再於 4位及6位羥基架以亞異丙基，而得化合物（Via )之工程，乙醯基之除去工程可依後述第B a 2工程①之條件進行反應而達成，亞異丙基架橋工程可依第A a 3工程之條件進行反應而達成。 (2 ) B 法 (2 — 1 ) a 法本方法爲製造R 5爲羥基之化合物（I )所用中間體（ ΧΧΠ)之製法。 -50 - 200413400 (第B a 1工程）本工程爲令化合物（XV)之3位羥基予以烷基化而製造化合物（XVI )之工程，可依第A a 1工程①之條件進行反應而達成。 (第B a 2工程）本工程爲令化合物（XVI)之2位予以脫保護，再將2 位胺基予以保護而製造化合物（XVII )之工程。 ① 脫保護反應本工程可在惰性溶劑中，於鹼性條件下，令化合物（ XVI)之2位三氟乙醯胺予以脫保護之工程。所使用溶劑爲例如，甲醇，乙醇等醇類；乙醚，四氫呋喃等醚類；乙腈等腈類，宜爲醇類（乙醇）。所使用鹼爲例如，碳酸氫鈉，碳酸氫鉀等鹼金屬碳酸氫化物類；氫氧化鈉，氫氧化鉀等鹼金屬氫氧化物；甲氧化鈉，乙氧化鈉等鹼金屬烷氧化物，宜爲鹼金屬氫氧化物。反應温度通常爲〇°C〜100°c，宜爲25°c〜80°c。反應時間通常爲3 0分〜2 4小時，宜爲1〜5小時。 ② 保護化反應本工程可在惰性溶劑中，於鹼存在下，與保護劑反應而達成。所使用溶劑爲例如，二氯甲烷，氯仿，四氯化碳等鹵化烴類；乙醚，二噚烷，四氫呋喃等醚類；乙腈等腈類，宜爲鹵化烴類，特宜爲二氯甲烷。所使用鹼爲例如，吡啶，二甲胺吡啶等吡啶類；三乙胺 200413400 ’三丁胺等三烷胺類；碳酸氫鈉，碳酸氫鉀等鹼金屬碳酸氫化物等，宜爲鹼金屬碳酸氫化物類（碳酸氫鈉）。所使用保護劑爲對後述第c 1工程葡糖基化不防礙者，宜爲三氯乙氧羰氯。反應温度通常爲一20°C〜60°C，宜爲（TC〜25°C。反應時間通常爲3 0分〜24小時，宜爲1〜5小時。反應終了後，本反應目的化合物（XVII )可依常法自反應混合物收集。例如，將反應混合物以溶劑稀釋，水洗後 ’分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，鲁蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，砍膠層析等精製。 (第B a 3工程）本工程爲令化合物（XVII)之4位及6位羥基保護基予以脫保護，而製造化合物（XVIII)之工程，可依上述（第 A a 5工程）之條件進行反應而達成。 (第B a 4工程）鲁本工程爲令化合物（XVIII)之1位烯丙基予以異構化後，製造6位羥基選擇保護之化合物（XIX )之工程。當R 4a有不飽和鍵結之場合，於以下工程中導入保護基時，爲以還原反應除去，可使用烯丙基或烯丙氧羰基，該烯丙基與1位烯丙基之差異而必需進行以下①之異構化反應，當R 4a無不飽和鍵結存在之場合，則可直接進行②之保護化反應。 -52 - 200413400 ① 1位烯丙基之異構化反應本工程可在惰性溶劑中，令化合物（XVIII )之1位烯丙基以金屬觸媒進行異構化反應。所使用溶劑爲例如，二氯甲烷，氯仿，四氯化碳等鹵化烴類；乙醚，二噚烷，四氫呋喃等醚類；乙酸乙酯等酯類 :乙腈等腈類，宜爲醚類，更宜爲四氫呋喃。所使用金屬觸媒爲例如鈀，鉻，銥等錯合物，宜爲（1， 5 —環辛二烯基）雙（甲二苯膦）銥（I )六氟磷酸鹽（ [Ir(COD)(PMePh2)2]PF6 )。反應温度通常爲0°C〜50°c，宜爲5°c〜30°c。反應時間通常爲1 0分〜24小時，宜爲3 0分〜8小時。 ② 6位羥基之保護化反應本反應可在惰性溶劑中，於鹼存在下，與保護劑反應而達成。所使用溶劑爲例如，二氯甲烷，氯仿，四氯化碳等鹵化烴類；乙醚，二噚烷，四氫呋喃等醚類；乙酸乙酯等酯類，宜爲二氯甲烷。所使用鹼爲例如，吡啶，二甲胺吡啶，三乙胺，N，N-二甲苯胺等有機鹽基類，宜爲毗啶。所使用保護劑，進行脫保護處理時，宜使用對6位羥基以高產率回收者，例如，第三丁氧羰氯等烷氧羰鹵，苄氧羰氯等芳氧羰鹵，烯丙氧羰氯等烯氧羰鹵，當R1()不存在不飽和鍵結時，宜爲苄氧羰氯，當R 4a存在不飽和鍵結時，宜爲烯丙氧羰氯。 -53 - 200413400 反應温度通常爲一50°C〜50°C，宜爲一l〇t：〜30°C。反應時間通常爲1 0分〜2 4小時，宜爲3 0分〜5小時。反應終了後，本反應目的化合物（XIX )可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第B a 5工程） φ 本工程爲令化合物（XIX )之4位羥基予磷氧化，而製造化合物（XX )之工程，可在惰性溶劑中，於鹼存在下，與磷氧化劑反應而達成。所使用溶劑爲例如，二氯甲烷，氯仿，四氯化碳等鹵化烴類；乙醚，四氫呋喃，二曙烷等醚類或含水之醚類；乙酸乙酯等酯類，宜爲鹵化烴類（二氯甲烷）。所使用鹼爲例如，吡啶，二甲胺吡啶，三乙胺，N,N —二甲苯胺，1 Η —四唑等有機鹼類，宜爲二甲胺吡啶。籲磷氧化劑，以式：（R12〇）2P ( = 〇）X (式中，R 12之定義如上，X爲氯，溴，碘等鹵原子，宜爲氯。）所表之磷醯鹵爲方法之一使用。磷醯鹵只要在後述第C a 5 工程或第C b 3工程中將憐酸酯化合物（xl )或（xliii ) 脫保護變換爲磷氧化合物（I)時，能使保護基R 1 2高產率容易除去即可，當R 4a不存在不飽和鍵結之場合，宜爲苯磷醯氯或苄磷醯氯，當R 4a存在不飽和鍵結之場合，其它 -54 - 200413400 方法宜以雙（烯丙氧基）（二異丙胺基）膦及四唑等鹼作成亞磷酸二烯丙酯，再以間氯過苯甲酸或以過氧化氫水來氧化’或以ο X ο n e等無機氧化劑氧化，而得磷酸二烯丙酯〇反應温度通常爲一20°C〜50°C，宜爲一1〇。(：〜30°C。反應時間通常爲1 0分〜24小時，宜爲3 0分〜5小時。反應終了後，本反應目的化合物（XX )可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (弟B a 6工程）本工程爲令化合物（XX )之1位保護基予以脫保護，而製造化合物（XXI )之工程。當R 4a不存在不飽和鍵結之場合，可依上述（第B a 4 工程）中①，令化合物（XX )之1位烯丙基以金屬觸媒來異構化，再水解來進行。當R 4a存在不飽和鍵結之場合，可將1位烯丙基予以異構化並水解來進行。異構化乙烯醚之水解可與鹽酸，硫酸，氫氟酸等無機酸 ;甲酸，對甲苯磺酸等有機酸作用，或在水中與碘作用來進行，宜爲在吡啶一水混合溶劑中與碘作用來進行，或用無機酸。 -55 - 200413400 反應温度通常爲0°c〜l〇〇°C，宜爲25°c〜45。(：。反應時間通常爲1 0分〜24小時，宜爲3 〇分〜5小時。反應終了後，本反應目的化合物（XXI )可依常法自反應混合物收集。例如，使用碘時，可在反應混合物中加入乙酸乙酯之不溶於水之有機溶劑，以硫代硫酸鈉水溶液，飽和碳酸氫鈉水溶液，飽和食鹽水洗淨後，分離含目的化合物之有機層’以無水硫酸鎂等乾燥後，蒸除溶劑而得。在使用無機酸時，重碳酸鈉溶液洗，以習知方法而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析鲁等精製。 (第B a 7工程）本工程爲製造中間體三氯乙醯亞胺酸酯體（XXII)之工程，將化合物（XXI ) 1位羥基，在惰性溶劑中，於鹼存在下，與三氯乙腈作用而達成。所使用溶劑爲例如，二氯甲烷，氯仿，四氯化碳等鹵化烴類；乙醚，二噚烷，四氫呋喃等醚類；乙酸乙酯等酯類 ;乙腈等腈類，宜爲鹵化烴類（二氯甲烷）。籲所使用鹼爲例如，1，8 —二吖雙環[5,4,0] — 7 - -f^一碳烯 (DBU)等有機鹼；或氫化鈉，碳酸鉀，碳酸鉋等無機鹼，宜爲碳酸鉋。反應温度通常爲一25°C〜50°C，宜爲〇°C〜25°C。反應時間通常爲1 0分〜24小時，宜爲3 0分〜2小時。反應終了後，本反應目的化合物（XXII)可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入 -56 - 200413400 乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。 (2 - 2 ) b 法本方法爲製造R 5爲烷氧基之化合物（I )所用中間體 (XXVIII)之製法。 (第B b 1工程）本工程爲將上述（第B a 1〜B a 3工程）所得化合物（ XVIII)之1位烯丙基予異構化後，而製造6位羥基予以選擇地保護之化合物（XXIII )之工程。籲當R 4a存在不飽和鍵結時，可依上述（第B a 4工程） ①之方法，將化合物（XVIII)之1位烯丙基以異構化爲必要，當R 4a不存在不飽和鍵結時，可直接進行保護化反應〇保護化反應可在在惰性溶劑中，於鹼存在下，與矽烷化劑反應而達成。所使用溶劑爲例如，二氯甲烷，氯仿，四氯化碳等鹵化烴類；乙醚，二噚烷，四氫呋喃等醚類·，乙腈等腈類，宜鲁爲二氯甲烷。所使用鹼爲例如，吡啶，二甲胺吡啶等毗啶類；三乙胺，三丁胺等三烷胺類；苯胺，N，N—二甲苯胺等苯胺類； 2，6 —二甲基吡啶等二甲基吡啶類，宜爲二甲胺吡啶。所使用矽烷化劑可使用如式：R 13 R 1 4 R 15 S i Y (式中，R13，R14及R15之定義如上，Y爲鹵原子或三氟甲磺醯基。）所示三烷矽烷化鹵或三烷矽烷三氟甲磺酸鹽，宜 -57 - 200413400 爲第三丁二甲矽烷化氯。反應温度通常爲0°C〜50°C，宜爲15t〜25°C。反應時間通常爲1〜24小時，宜爲1〜8小時。反應終了後，本反應目的化合物（XXIII )可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 · (第B b 2工程）本工程爲令化合物（XXIII )之4位羥基予以磷氧化，而製造化合物（XXIV )之工程，可依上述（第b a5工程）之條件進行反應而達成。 (第B b 3工程）本工程爲令化合物（XXIV )之6位保護基除去，而製造化合物（XXV )之工程，可在惰性溶劑中，於酸性條件下水解來達成。籲水解所使用酸爲如鹽酸，硫酸，氫氟酸等無機酸，乙酸，草酸，對甲苯磺酸等有機酸，宜爲鹽酸，又宜爲3mol/L 鹽酸水溶液。所使用溶劑爲如二噚院，四氫呋喃等水溶性溶劑，宜爲四氫呋喃。反應温度通常爲20°C〜80°C，宜爲2CTC〜50°C。反應時間通常爲30分〜24小時，宜爲1〜8小時。 -58 - 200413400 反應終了後，本反應目的化合物（XXV )可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第B b 4工程）本工程爲令化合物（XXV)之6位羥基予烷化，而製造化合物（XXVI)之工程，可依以下①之方法來達成。當R 5b爲甲基時，可使用②之方法。 ①當1151)爲（：1一 C6烷基之場合本工程可在惰性溶劑中，於鹼或氧化銀（II)(AgO)存在下，令化合物（XXV )與烷化劑反應來達成。反應所用溶劑只要不影響反應，而能溶解原料者則無特定，例如，己烷，庚烷，石油英等脂肪族烴類；苯，甲苯，二甲苯等芳香族烴類；二氯甲烷，氯仿，四氯化碳，二氯乙烷，氯苯等鹵化烴類；乙酸乙酯，乙酸丙酯，碳酸二乙酯等酯類；乙醚，二異丙醚，四氫呋喃，二卩等烷等醚類 ;乙腈，異丁腈等腈類；甲醯胺，N，N —二甲基甲醯胺， N，N —二甲基乙醯胺等醯胺類，宜爲醚類。所使用鹼爲例如，碳酸鈉，碳酸鉀等鹼金屬碳酸鹽類；碳酸氫鈉，碳酸氫鉀等鹼金屬碳酸氫鹽類；氫化鈉’氫化鉀等鹼金屬氫化物類；N —甲基嗎啉，三乙胺，三丁胺，二異丙基乙胺，二環己胺，N-甲哌啶，吡啶，皮考林，4 — -59 - 200413400 (N，N -二甲胺基）吡啶，2，6—二（第三丁基）一4 —甲基吡啶，N，N -二甲苯胺，N，N -二乙基苯胺，1，5 -二吖雙環 [4.3.0]壬一5—烯（〇38 1^)，1，4-二口丫雙環[2.2.2]辛院（ DABCO) ，1，8—二吖雙環[5.4.0]十一碳一7—烯（〇 BU)等有機鹼類。宜爲有機鹼類，更宜爲DBN或DB U。所使用烷化劑爲例如，式：R 5 b Z (式中，R 5 b之定義如上，Z爲碘原子，溴原子，氯原子，鹵甲苯磺醯氧基或甲磺醯氧基）。反應温度通常爲0°C〜100°C下進行，宜爲0°C〜30。(：。反應時間通常爲1 0分〜2 4小時，宜爲1〜1 8小時。 ②R5b爲甲基之場合本工程可在惰性溶劑中，於鹼存在下，令化合物（XXV )與四氟硼酸三甲鍚反應而達成。所使用溶劑爲例如，乙醚，二噚烷，四氫呋喃等醚類；二氯甲垸，氯仿，四氯化碳等鹵化烴；甲醯胺，N，N—二甲基甲醯胺，N，N—二甲基乙醯胺等醯胺類，宜爲二氯甲烷。所使用驗宜爲2,6 —二一第二丁基一 4 —甲基[I比Π定。反應温度通常爲—50°C〜l〇〇°C下進行，宜爲〇°c〜30°C。反應時間通常爲1〜2 4小時，宜爲2〜5小時。反應終了後，本反應目的化合物（XX VI )可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層’以無水硫酸錶寺乾燥後，蒸除溶劑而得。 -60 - 200413400 所得化合物視需要可依常法，例如，再結晶，矽膠層析等而精製。 (第B b 5工程）本工程爲令化合物（XXVI)之1位保護基予以脫保護來製造化合物（XXVII )之工程，可依上述（第B a 6工程）之條件進行反應來達成。 (第B b 6工程）本工程爲製造中間體三氯乙醯亞胺酸酯體（XXVIII)之工程，可依上述（第B a 7工程）之條件進行反應而達成 _ 〇 (2 — 3 ) c 法本方法爲製造R5爲氫原子或鹵原子之化合物（I)所用中間體（XXXI)之製法。 (第B c 1工程）本工程爲令上述（第B b 1〜B b 3工程）所得化合物（ XXV )之6位羥基變換爲鹵原子或氫原子，而製造化合物 (XXIX )之工程。 _ (第B c 1 — 1工程）本工程爲令化合物（XXIX)中R5e爲鹵原子場合之製造方法，可依以下①，②或③法進行。 ①當115(：爲氟原子之場合本工程可在惰性溶劑中，令化合物（XXV )與氟化劑反應而達成。所使用溶劑爲例如，二氯甲烷，氟三氯甲烷等鹵化烴類 -61 - 200413400 •，乙醚，1,2 —二甲氧乙烷等醚類，宜爲二氯甲烷。所使用氟化劑爲例如，三氟化二乙胺硫（DAST)。反應温度通常爲一 78C〜25C下進行，宜爲〜25。〇。反應時間通常爲1〜1 8小時，宜爲1〜5小時。 ② 當R5e爲氯原子或溴原子之場合本工程可在惰性溶劑中，令化合物（X X V )與三氯化磷 ’三溴化磷’磷醯化三氯，磷醯化三溴，亞磺醯氯或亞磺醯溴反應而達成。所使用溶劑宜爲二氯甲烷，氯仿，四氯化碳等鹵化烴類 0 反應温度通常爲一50°c〜5(TC下進行，宜爲—1(rc〜3〇t：〇反應時間通常爲1〜1 8小時，宜爲1〜5小時。 ③ 當R 5e爲碘原子之場合本工程可在惰性溶劑中，令化合物（XXV )與碘及三苯膦反應而達成。反應所用溶劑只要不影響反應，而能溶解原料者則無特定，例如，己烷，庚烷，石油英等脂肪族烴類；苯，甲苯，二甲苯等芳香族烴類；二氯甲烷，氯仿，四氯化碳，二氯乙烷，氯苯等鹵化烴類；乙酸乙酯，乙酸丙酯，碳酸二乙酯等酯類；乙醚，二異丙醚，四氫呋喃，二噚烷等醚類 ;甲醇，乙醇等醇類；甲醯胺，N，N —二甲基甲醯胺， N，N —二甲基乙醯胺等醯胺類，宜爲醚類。反應温度通常爲一50〜100°C下進行，宜爲〇t〜30°C。 -62 - 200413400 反應時間通常爲1〜1 8小時，宜爲1〜5小時。反應終了後，本反應目的化合物（XXIX )可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第B c 1 — 2工程）本工程中，當化合物（XXIX)中R5。爲氫原子時，可令 _ 上述（第B C 1 — 1工程）②所得R 爲溴原子之化合物，於惰性溶劑中，與四丁錫氫化物或氫化鋰鋁反應來進行。所使用溶劑爲例如，己烷，庚烷，石油英等脂肪族烴類 ;苯，甲苯，二甲苯等芳香族烴類；乙醚，二異丙醚，四氫呋喃，二噚烷等醚類，宜爲醚類。R9 and R1G are the same or different, each is a hydrogen atom, Cf C6 alkyl or C 6-c 1 0 aryl. R11 is a 1-propyl group. R13, R14, and R15 are the same or different, and each is a CpC * alkyl group or a C 6 -C i aryl group. R16 is the Ci-C6 courtyard. R17 is the Ci-1 C6 courtyard. The production process of the compound (VII) of the present invention is as follows: A to η method. (1) Method A is -39-200413400 method for manufacturing intermediates (XI), (XIa) or (χιν). (2) Method B is a process for manufacturing intermediates (XXII), (XXVIII) and (XXXI). According to the types of R 5, three methods of method a, method b, and method c are described. (3) Method C is to condense the intermediate (XI), (XIa) or (XIV) with the intermediate (XXII), (XXVIII) or (XXXI) to produce the target compound (XLI), (XLIV) or (XXXIX). ) Project. (4) Method D is a process for producing an intermediate (XLVII), which is condensed with an intermediate (χχπ), (XXVIII), or (XXXI) to produce a target compound (l). (5) The E method is a process for producing an objective compound (Lxn) in which Q is an ethoxy group. (6) The F method is a process for producing an objective compound (LXXII) in which Q is a methylene group. (7) The G method is a process for producing an objective compound (LXXVIII) in which Q is trimethylenedioxy. (8) The hydrazone method is a process for producing an intermediate in which R1 is decyl (xiVa). The following is a description of each process. (1) Method A (the A a 1 project) This project is to alkylate the 3-position of a monoacetone-D-glucose compound (π) (including the introduction of alkenyl and alkynyl groups. The following is the manufacturing process In the description, 'has the same definition.) Or in the process of producing a fluorinated compound (III), alkylation is achieved by the following (a) method, and fluorination is achieved by the following (b) method -40-200413400. (a) Alkylation This project is achieved by reacting compound (II) with an alkylating agent in an inert solvent in the presence of a base. The solvents used are, for example, ethers such as dioxane, tetrahydrofuran; fluorenamines such as formamidine, dimethylformamide; halogenated hydrocarbons such as dichloromethane, preferably dimethylformamide. The bases used are, for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; lithium alkanes such as n-butyllithium and tertiary butyl lithium; and alkali metal hydrides such as potassium hydride and sodium hydride. The alkylating agent used is, for example, a halogenated hydrocarbon, a sulfonate, and preferably a bromide (R 2 B r) or a mesylate (R 2SO2M e). The reaction temperature is usually 0 ° C to 100 ° C, and preferably 0 ° C to 60 ° C. 'The reaction time varies depending on the reaction temperature, raw materials, reagents, solvents used, etc. It is usually 20 minutes to 48 hours, preferably 2 to 24 hours. After completion of the reaction, the target compound of the present reaction can be collected from the reaction mixture by a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding an ethyl acetate-insoluble organic solvent, washing with water, separating the organic layer containing the target compound, drying over anhydrous magnesium sulfate, and evaporating the solvent. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (b) Alkylation This project is to achieve the reaction of compound (II) with a halogenating agent such as carboxylic acid or acid salt in the presence or absence of a condensing agent and a base in an inert solvent. -41-200413400 Used The solvent is, for example, ethers such as tetrahydrofuran and dioxane; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; and amidines such as n, n-dimethylformamide, preferably dichloromethane. The condensing agent used in the carboxylic acid reaction is 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1- [3- (dimethylamino) propyl 3-ethyl Carbodiimides such as carbodiimide hydrochloride (WSCI) are preferably 1,3-dicyclohexylcarbodiimide. The base used in the acidification reaction is pyridine, dimethylamine pyridine, triethylamine and other organic bases, preferably 4-dimethylamine pyridine. The halogenating agent used is a carboxylic acid of the formula: R2′〇H, or a formula: R2′C 1 (where R2 ′ is an intermediate group of R2 as defined by R2, sulfonyl or alkynyl). The chlorine . When the halogenating agent contains a hydroxyl group or an oxy group, the group may be protected, for example, the oxy group is protected as an acetal group. The reaction temperature is usually 0 ° C to 100 ° C, preferably 15 ° C to 25 ° C (room temperature). The reaction time is usually 20 minutes to 24 hours, preferably 1 to 5 hours. # After the reaction is completed, the target compound of this reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is filtered, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project A a 2) -42-200413400 This project is a project to obtain compound (IV) by heating compound (III) in an allyl alcohol solvent in the presence of hydrochloric acid gas. The reaction temperature is usually from 0 ° c to the reflux temperature of the solvent, and preferably from room temperature to 80 ° c. The reaction time is usually 20 minutes to 24 hours, and preferably 1 to 5 hours. (Project A a 3) This project is a process in which compound (V) is obtained by using isopropylidene at the 4- and 6-position hydroxyl groups of compound (IV). This project can be achieved by reacting compound (IV) with 2,2-dimethoxypropane in an inert solvent in the presence of an acid catalyst. The solvent used is, for example, amidines such as dimethylformamide. The acid catalysts used are p-toluenesulfonic acid, sulfonic acid and the like. The reaction temperature is usually from room temperature to 50 ° C. The reaction time is usually 20 minutes to 24 hours. After the reaction is completed, the target compound (V) of the reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project A a 4) This project is to alkylate the 2-hydroxy group of compound (V) to obtain compound (VI), which can be achieved by the reaction of project A a 1. (Project A a 5) -43-200413400 This project is a process for producing a compound (V Π) by deprotecting the isopropylidene groups at the 4- and 6-position hydroxyl groups of the compound (VI). This project is achieved by reacting compound (VI) with an acid catalyst or N B S in an alcohol solvent. The solvents used are, for example, alcohols such as methanol and ethanol. The acid catalysts used are organic acids such as p-toluenesulfonic acid and sulfonic acid; inorganic acids such as hydrochloric acid and sulfuric acid. The reaction temperature is usually 0 ° C ~ 50 ° C, preferably room temperature. The reaction time is between 6 minutes and 24 hours, preferably 30 minutes. After completion of the reaction, the target compound (VII) of the present reaction can be collected from the reaction mixture by a conventional method. For example, the reaction mixture is concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project A a 6) This project is a process for converting the double bond of the allyl group of the compound (VII) to an enol ether type to produce the compound (VIII). This project can be achieved by reacting compound (vii) with an alkali or iridium complex in an inert solvent. The solvents to be used are, for example, ethers such as tetrahydrofuran and dioxane; sulfenes such as dimethylarsine; when a base is used, dimethylarylene is preferred; when an iridium complex is used, tetrahydrofuran is preferred. The test used is, for example, an alkali metal alkoxide such as potassium third butoxide, sodium methoxide, sodium ethoxide, etc., preferably potassium third butoxide. -44-200413400 The iridium complex used is, for example, (1,5-cyclooctyldienyl) bis (methyldiphenylphosphine) iridium (I) hexafluorophosphate. The reaction temperature is usually from room temperature to the solvent heating reflux temperature when used, and when the iridium complex is used, it is usually ~ 80. (:, Preferably room temperature. When using a base, the reaction time is usually 1 hour to 24 hours, preferably 1 hour. After the reaction is completed, the target compound (VIII) of the reaction can be collected from the reaction mixture according to a conventional method. For example, The reaction mixture was concentrated, and ethyl acetate, an insoluble organic solvent was added, and after washing with water, the organic layer containing the target compound was separated, dried over anhydrous magnesium sulfate, etc., and the solvent was distilled off to obtain the obtained compound. For example, recrystallization, purification by silica gel chromatography, etc. (Project A a 7) This project is a process of manufacturing compound (IX) by protecting the first hydroxy group of the diol of compound (VIII) with a silane group. This project is an order Compound (VIII) is achieved by reacting with a silylating agent in the presence of a base in an inert solvent. The solvents used are, for example, ethers such as tetrahydrofuran, dioxane; halogenated solvents such as dichloromethane, chloroform, and carbon tetrachloride The hydrocarbon is preferably dichloromethane or tetrahydrofuran. The base used is, for example, organic salts such as pyridine, dimethylamine pyridine, triethylamine, etc. The silylating agent used is, for example, chlorinated The third selenium selenium foundation is a third-grade dentistry foundation. 200413400 The reaction temperature is usually 0 ° C ~ 80 ° C, preferably room temperature. The reaction time is usually 6 minutes to 24 hours. After the reaction is completed, this reaction The target compound (IX) can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is concentrated, and ethyl acetate is added to the water-insoluble organic solvent. After washing with water, the organic layer containing the target compound is separated and dried over anhydrous magnesium sulfate Then, it is obtained by distilling off the solvent. The obtained compound can be purified according to ordinary methods, for example, recrystallization, silica gel chromatography, etc. (Project A a 8) This project is to make the secondary hydroxyl group of compound (IX) a silyl group. Protection, and the process of producing compound (X). This project can be achieved by reacting compound (IX) with an amidine and an alcohol in an inert solvent in the presence of a base. The solvent used is, for example, tetrahydrofuran Ethers such as dioxane; aromatic hydrocarbons such as benzene, toluene, xylene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, etc. The base used is, for example, pyridine , Second Organic bases such as pyridine, triethylamine, etc. The amylating agent used is. The alcohol used is allyl alcohol. The reaction temperature is usually -20 ° C ~ 50 ° C, preferably 0 ° C. The reaction time is after adding After adding the alcohol, it is usually 10 minutes to 1 hour, preferably 10 minutes, and after adding the alcohol, the reaction time is usually 10 minutes to 1 hour, preferably 1 hour. -46-200413400 After completion of the reaction, the target compound (x) of the reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is concentrated, and ethyl acetate is added to the water-insoluble organic solvent. After washing with water, the organic layer containing the target compound is separated. It is obtained by drying with anhydrous magnesium sulfate, etc., and then distilling off the solvent. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, etc., if necessary. (Project A a 9) This project is a process for deprotecting the silane protecting group of compound (X) and producing a primary alcohol compound (XI). This project can be achieved by reacting the compound (X φ) with an acid catalyst in an inert solvent. The solvents used are, for example, ethers such as tetrahydrofuran and dioxane; nitriles such as acetonitrile; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, and chlorobenzene. The acid catalysts used are, for example, inorganic acids such as hydrochloric acid and hydrofluoric acid; organic acids such as p-toluenesulfonic acid. The reaction temperature is usually 20 ° C ~ 50 ° C, preferably room temperature. The reaction time is usually 6 minutes to 2 hours, preferably 15 minutes. After the completion of the reaction, the target compound (XI) of the reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Brother A a 10 Project) -47-200413400 This project is to deprotect the silane protecting group of compound (x), and then simultaneously deprotect the ortho-isomerized enol ether to produce a primary alcohol compound (XIa) Of works. This project can be achieved according to the more severe reaction conditions of Project A a 9, such as a longer reaction time. The reaction time is usually 4 hours to 24 hours, and preferably 10 hours to 16 hours. After the reaction is completed, the target compound (XIa) of the reaction can be collected from the reaction mixture by a conventional method. For example, the reaction mixture is concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project A b 1) This project is to produce compound (XII) by reducing the allyl double bond of compound (VI) by oxidative cleavage to obtain aldehyde. This project is achieved by reacting compound (VI) with an oxidant in an inert solvent, and then reacting with a reducing agent in an inert solvent. The solvent used in the oxidation reaction is, for example, a mixed solvent of ethers such as tetrahydrofuran and dioxane and water, and the solvent used in the reduction reaction is, for example, alcohols such as methanol and ethanol. The oxidant used is, for example, a combination of tungsten tetraoxide and sodium periodate. The reducing agent used is, for example, a metal hydride such as lithium aluminum hydride or sodium borohydride, preferably sodium borohydride. The reaction temperature is usually 0 ° C ~ 50 ° C, preferably room temperature. -48-200413400 The reaction time is usually 6 minutes to 24 hours. After the reaction is completed, the target compound (XII) of the reaction can be collected from the reaction mixture by a conventional method. For example, the reaction mixture is concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project A b 2) This project is a process for converting compound (XII) into a phosphite and oxidizing it to produce compound (XIII). This project can be achieved by reacting compound (XII) with diisopropyl amino phosphate in the presence of a weak acid 1H-tetrazole in an inert solvent, and then reacting with an oxidant in an inert solvent. The solvents used are, for example, ethers such as tetrahydrofuran and dioxane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, and chlorobenzene. The oxidant used is, for example, a peroxide such as hydrogen peroxide, m-chloroperbenzoic acid, oxone, and the like. The reaction temperature is usually 0 ° C ~ 100 ° C, preferably room temperature. _ The reaction time is usually 6 minutes to 24 hours. After completion of the reaction, the target compound (XIII) of the present reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated and dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound can be purified by a conventional method, for example, recrystallization, silica gel chromatography, etc., if necessary. -49-U4134〇〇 (Project A b 3) This project is to deprotect the 4- and 6-hydroxyl-bridged propylidene groups of compound (XII), and the process of manufacturing compound (XIV) can be carried out according to the A a 5 project conditions were achieved by reaction. (Project A c 1) This project is to obtain a compound (Via) by making isopropylidene at the 4- and 6-hydroxy groups of a known compound (LI), and then allylating the 1-hydroxy group. The isopropylidene bridge project can be achieved according to the conditions of the Aa 3 project, and the allylization project can be achieved according to the conditions of the allylization in the A a 1 project. (Project A c 2) This project is a process for pre-alkylating two hydroxyl groups of compound (Via) to obtain compound (VIb). The reaction can be achieved by performing reactions similar to the conditions of project A a 1 (the A c 3 Process) This process is a process of removing 4 ethenyl groups of a known compound (LII), and then using isopropylidene at the 4- and 6-position hydroxyl groups to obtain a compound (Via). The reaction can be achieved according to the conditions of the Ba 2 project ① described later, and the isopropylidene bridge construction can be achieved by the reactions according to the conditions of the A a 3 project. (2) Method B (2-1) Method a This method is a method for producing an intermediate (XΠ) used for the compound (I) in which R 5 is a hydroxyl group. -50-200413400 (Project B a 1) This project is a process for making compound (XVI) by alkylating the 3-position hydroxyl group of compound (XV). It can be achieved by performing the reaction according to the conditions of Project A a 1 . (Project B a 2) This project is a process for producing compound (XVII) by deprotecting the 2-position of compound (XVI) and then protecting the amine group at 2-position. ① Deprotection reaction This project can deprotect the trifluoroacetamide of compound (XVI) in the inert solvent under alkaline conditions. The solvents used are, for example, alcohols such as methanol and ethanol; ethers such as diethyl ether and tetrahydrofuran; and nitriles such as acetonitrile, preferably alcohols (ethanol). The bases used are, for example, alkali metal hydrides such as sodium bicarbonate and potassium bicarbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; It is an alkali metal hydroxide. The reaction temperature is usually 0 ° C to 100 ° c, preferably 25 ° c to 80 ° c. The reaction time is usually 30 minutes to 24 hours, preferably 1 to 5 hours. ② Protective reaction This project can be achieved by reacting with a protective agent in an inert solvent in the presence of a base. The solvent used is, for example, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride; ethers such as diethyl ether, dioxane, tetrahydrofuran; nitriles such as acetonitrile, etc., preferably halogenated hydrocarbons, particularly dichloromethane. The bases used are, for example, pyridines such as pyridine, dimethylamine pyridine; triethylamine 200413400 'trialkylamines such as tributylamine; alkali metal hydrides such as sodium bicarbonate and potassium bicarbonate, etc., preferably alkali metal carbonates Hydrides (sodium bicarbonate). The protective agent used is one which does not prevent the glycosylation of the c1 project described later, and is preferably trichloroethoxycarbonyl chloride. The reaction temperature is usually from 20 ° C to 60 ° C, preferably (TC to 25 ° C. The reaction time is usually from 30 minutes to 24 hours, preferably from 1 to 5 hours. After the reaction, the target compound of the reaction (XVII ) Can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is diluted with a solvent, washed with water, and 'the organic layer containing the target compound is separated, dried with anhydrous magnesium sulfate, etc., and then the solvent is distilled off to obtain the obtained compound as needed. Refine according to the usual method, for example, recrystallization, gel chromatography, etc. (Project B a 3) This project is to produce the compound (XVIII) by deprotecting the 4- and 6-hydroxy protecting groups of the compound (XVII). The project can be achieved by carrying out the reaction according to the conditions described above (Project A a 5). (Project B a 4) The Reuben Project is to beomerize 1-allyl of compound (XVIII) to produce 6 Process for selecting a protected compound (XIX) at the hydroxyl group. When R 4a has an unsaturated bond, when a protective group is introduced in the following process, in order to remove it by reduction reaction, an allyl or allyloxycarbonyl group can be used. Difference between allyl and 1-allyl The following isomerization reaction must be carried out. When R 4a has no unsaturated bond, the protection reaction of ② can be directly carried out. -52-200413400 ① Isomerization reaction of allyl in this project The allyl group at the 1-position of the compound (XVIII) can be isomerized with a metal catalyst in an inert solvent. The solvent used is, for example, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride; ether, Ethers such as dioxane and tetrahydrofuran; esters such as ethyl acetate: nitriles such as acetonitrile, preferably ethers, more preferably tetrahydrofuran. The metal catalyst used is, for example, a complex of palladium, chromium, iridium, etc., preferably (1, 5-cyclooctadienyl) bis (methyldiphenylphosphine) iridium (I) hexafluorophosphate ([Ir (COD) (PMePh2) 2] PF6). The reaction temperature is usually 0 ° C ~ 50 ° c, preferably 5 ° c ~ 30 ° c. The reaction time is usually 10 minutes to 24 hours, preferably 30 minutes to 8 hours. ② Protection reaction of the hydroxyl group at the 6 position This reaction can be performed in an inert solvent and in a base. In the presence, it is achieved by reaction with a protecting agent. The solvents used are, for example, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc. Ethers such as diethyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate, preferably dichloromethane. The bases used are, for example, pyridine, dimethylamine pyridine, triethylamine, N, N-xylamine, and the like. The base is preferably pyridine. When the protecting agent is used for deprotection treatment, it is suitable to use a high-yield recovery of the hydroxyl group at the 6-position, for example, an alkoxycarbonyl halide such as a third butoxycarbonyl chloride, and a benzyloxycarbonyl chloride. Allyloxycarbonyl halides such as aryloxycarbonyl halide, allyloxycarbonyl chloride, etc. When R1 () does not have unsaturated bonds, it is preferably benzyloxycarbonyl chloride, and when R 4a has unsaturated bonds, it is preferably allyl. Oxycarbonyl chloride. -53-200413400 The reaction temperature is usually -50 ° C ~ 50 ° C, preferably 10 °: ~ 30 ° C. The reaction time is usually 10 minutes to 24 hours, and preferably 30 minutes to 5 hours. After the reaction is completed, the target compound (XIX) of the reaction can be collected from the reaction mixture according to a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding ethyl acetate, an insoluble organic solvent, washing with water, separating the organic layer containing the desired compound, drying over anhydrous magnesium sulfate, and then distilling off the solvent. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project B a 5) φ This project is to oxidize the 4-hydroxy group of compound (XIX) with phosphorus, and to produce compound (XX), it can be achieved by reacting with phosphorus oxidant in an inert solvent in the presence of a base. . The solvents used are, for example, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride; ethers such as diethyl ether, tetrahydrofuran, dioxane or water-containing ethers; esters such as ethyl acetate, preferably halogenated hydrocarbons ( Methylene chloride). The base to be used is, for example, organic bases such as pyridine, dimethylamine pyridine, triethylamine, N, N-xylylamine, 1-tetrazolium, etc., preferably dimethylamine pyridine. Phosphorus oxidants are represented by the formula: (R12〇) 2P (= 〇) X (wherein R 12 is as defined above, X is a halogen atom such as chlorine, bromine, iodine, etc., preferably chlorine.) Use one of the methods. Phosphonium halide can make the protective group R 1 2 high-yield if the phosphoric acid ester compound (xl) or (xliii) is deprotected and converted to the phosphorus oxy compound (I) in the C a 5 or C b 3 process described later. The rate can be easily removed. When R 4a does not have unsaturated bonds, it should be phenylphosphine chloride or benzylphosphonium chloride. When R 4a has unsaturated bonds, the other -54-200413400 methods should be double (Allyloxy) (diisopropylamino) phosphine and tetrazole are used to form diallyl phosphite, and then oxidized with m-chloroperbenzoic acid or hydrogen peroxide water, or ο X ο ne and other inorganic The oxidant is oxidized to obtain diallyl phosphate. The reaction temperature is usually -20 ° C ~ 50 ° C, preferably -10. (: ~ 30 ° C. The reaction time is usually 10 minutes to 24 hours, preferably 30 minutes to 5 hours. After the reaction is completed, the target compound (XX) of the reaction can be collected from the reaction mixture by a conventional method. For example, After the reaction mixture was neutralized, concentrated, ethyl acetate-insoluble organic solvent was added, and after washing with water, the organic layer containing the target compound was separated, dried over anhydrous magnesium sulfate, etc., and the solvent was distilled off to obtain the obtained compound as needed. Refine according to the usual method, for example, recrystallization, silica gel chromatography, etc. (Brother B a 6 Project) This project is the process of deprotecting the protecting group of compound (XX) to produce compound (XXI). When R When there is no unsaturated bond in 4a, the allyl group at the 1-position of compound (XX) can be isomerized with metal catalyst and then hydrolyzed according to ① in the above (Ba 4 project). When R In the case of unsaturated bond 4a, the allyl group 1 can be isomerized and hydrolyzed. The hydrolysis of isomerized vinyl ether can be performed with inorganic acids such as hydrochloric acid, sulfuric acid, hydrofluoric acid, formic acid, p-toluenesulfonic acid, etc. Organic acids such as acids or iodine in water The reaction is preferably performed with iodine in a pyridine-water mixed solvent, or with an inorganic acid. -55-200413400 The reaction temperature is usually 0 ° c ~ 100 ° C, preferably 25 ° c ~ 45. : The reaction time is usually 10 minutes to 24 hours, preferably 30 minutes to 5 hours. After the reaction is completed, the target compound (XXI) of the reaction can be collected from the reaction mixture according to a conventional method. For example, when using iodine, The reaction mixture was added with ethyl acetate, an insoluble organic solvent, washed with an aqueous sodium thiosulfate solution, a saturated sodium bicarbonate aqueous solution, and a saturated saline solution, and then the organic layer containing the target compound was separated and dried over anhydrous magnesium sulfate. It is obtained by distilling off the solvent. When using an inorganic acid, it is washed with a sodium bicarbonate solution and obtained by a conventional method. If necessary, the obtained compound can be purified according to a conventional method, for example, recrystallization, silica gel chromatography, etc. (Section B a 7 Project) This project is a process for manufacturing the intermediate trichloroacetamidoimide (XXII). The compound (XXI) is reacted with the hydroxyl group at the 1-position in an inert solvent in the presence of a base to react with trichloroacetonitrile. Achieved. For example, dichloromethane, chloroform, carbon tetrachloride and other halogenated hydrocarbons; ethers, dioxane, tetrahydrofuran and other ethers; ethyl acetate and other esters; nitriles such as acetonitrile, preferably halogenated hydrocarbons (dichloromethane ). The base to be used is, for example, an organic base such as 1,8-diazepine bicyclic [5,4,0] — 7--f ^ -carbene (DBU); or an inorganic base such as sodium hydride, potassium carbonate, or carbonic acid shavings. Alkali, preferably carbonic acid shaving. The reaction temperature is usually -25 ° C ~ 50 ° C, preferably 0 ° C ~ 25 ° C. The reaction time is usually 10 minutes to 24 hours, preferably 30 minutes to 2 hours. After the reaction is completed, the target compound (XXII) of the present reaction can be collected from the reaction mixture by a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding -56-200413400 ethyl acetate insoluble organic solvent, washing with water, separating the organic layer containing the target compound, drying with anhydrous magnesium sulfate, etc. Got. (2-2) method b This method is a method for producing an intermediate (XXVIII) used for the compound (I) in which R 5 is an alkoxy group. (Project B b 1) This project is to pre-isomerize the 1-allyl group of the compound (XVIII) obtained in the above (Projects B a 1 to B a 3), and to selectively protect the 6-hydroxy group. Engineering of Compound (XXIII). When R 4a is unsaturated, it is necessary to make isomerization of the allyl group of compound (XVIII) necessary according to the method of the above (Ba 4 project) ①. When R 4a is not unsaturated, When bonding, the protection reaction can be directly performed. The protection reaction can be achieved by reacting with a silylating agent in an inert solvent in the presence of a base. The solvents used are, for example, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethers such as diethyl ether, dioxane, tetrahydrofuran, and nitriles such as acetonitrile, preferably dichloromethane. The bases used are, for example, pyridines such as pyridine, dimethylamine pyridine; trialkylamines such as triethylamine, tributylamine; anilines such as aniline, N, N-xylylamine; 2,6-dimethyl Dimethylpyridines such as pyridine are preferably dimethylamine pyridine. The silylating agent used can be used as formula: R 13 R 1 4 R 15 S i Y (wherein R13, R14 and R15 have the same definitions as above, Y is a halogen atom or trifluoromethanesulfonyl.) Silane halide or trioxane silane trifluoromethanesulfonate, preferably -57-200413400 is tertiary dimethyl dimethylsilyl chloride. The reaction temperature is usually 0 ° C ~ 50 ° C, preferably 15t ~ 25 ° C. The reaction time is usually 1 to 24 hours, preferably 1 to 8 hours. After the reaction is completed, the target compound (XXIII) of the present reaction can be collected from the reaction mixture by a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding ethyl acetate, an insoluble organic solvent, washing with water, separating the organic layer containing the desired compound, drying over anhydrous magnesium sulfate, and then distilling off the solvent. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. · (Project B b 2) This project is to oxidize the 4-hydroxy group of the compound (XXIII) with phosphorus, and the process for producing the compound (XXIV) can be achieved by performing the reaction according to the conditions described above (Project b a5). (Project B b 3) This process is to remove the protecting group at position 6 of compound (XXIV), and to produce compound (XXV), it can be accomplished by hydrolysis in an inert solvent under acidic conditions. The acids used in the hydrolysis are inorganic acids such as hydrochloric acid, sulfuric acid, hydrofluoric acid, organic acids such as acetic acid, oxalic acid, p-toluenesulfonic acid, etc., preferably hydrochloric acid, and also a 3mol / L aqueous hydrochloric acid solution. The solvent used is a water-soluble solvent such as Er'anyuan and tetrahydrofuran, and is preferably tetrahydrofuran. The reaction temperature is usually 20 ° C ~ 80 ° C, preferably 2CTC ~ 50 ° C. The reaction time is usually 30 minutes to 24 hours, preferably 1 to 8 hours. -58-200413400 After the reaction is completed, the target compound (XXV) of the reaction can be collected from the reaction mixture according to a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding ethyl acetate, an insoluble organic solvent, washing with water, separating the organic layer containing the desired compound, drying over anhydrous magnesium sulfate, and then distilling off the solvent. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project B b 4) This project is to alkylate the 6-hydroxy group of compound (XXV), and the process of producing compound (XXVI) can be achieved by the following method (1). When R 5b is methyl, the method of ② can be used. ① When 1151) is (: 1-C6 alkyl group) This project can be achieved by reacting the compound (XXV) with an alkylating agent in an inert solvent in the presence of a base or silver (II) (AgO). Reaction The solvent used is not specific as long as it does not affect the reaction, and it can dissolve the raw materials, for example, aliphatic hydrocarbons such as hexane, heptane, petroleum spirit; aromatic hydrocarbons such as benzene, toluene, xylene; methylene chloride, chloroform, Halogenated hydrocarbons such as carbon tetrachloride, dichloroethane, and chlorobenzene; esters such as ethyl acetate, propyl acetate, and diethyl carbonate; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; Nitriles such as acetonitrile, isobutyronitrile, and other amines such as formamidine, N, N-dimethylformamide, and N, N-dimethylacetamide, are preferably ethers. The base used is, for example, Alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium bicarbonate; Alkali metal hydrides such as sodium hydride and potassium hydride; N-methylmorpholine, triethylamine, Tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, picolin, 4 -59-200413400 (N , N-dimethylamino) pyridine, 2,6-bis (third butyl) -4methylpyridine, N, N-dimethyltoluidine, N, N-diethylaniline, 1,5-di Acridine bicyclo [4. 3. 0] noni 5-ene (〇38 1 ^), 1,4-dimouth bicyclo [2. 2. 2] Xin Yuan (DABCO), 1, 8-diazine bicyclic ring [5. 4. 0] Organic bases such as undecyl-7-ene (〇 BU). It is preferably an organic base, more preferably DBN or DB U. The alkylating agent used is, for example, the formula: R 5 b Z (wherein, R 5 b is as defined above, Z is an iodine atom, a bromine atom, a chlorine atom, a tosylsulfonyloxy group or a methylsulfonyloxy group). The reaction temperature is usually 0 ° C ~ 100 ° C, and preferably 0 ° C ~ 30. (:. The reaction time is usually 10 minutes to 24 hours, preferably 1 to 18 hours. ② When R5b is a methyl group In this project, the compound (XXV) and tetrafluoride can be made in an inert solvent in the presence of a base. This is achieved by the reaction of trimethylammonium borate. The solvents used are, for example, ethers such as diethyl ether, dioxane, tetrahydrofuran; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride; formamidine, N, N-dimethyl Methylamine, N, N-dimethylacetamide and other amines are preferably dichloromethane. The test used is preferably 2,6-di-second-butyl-4-methyl [I The reaction temperature is usually from -50 ° C to 100 ° C, preferably from 0 ° c to 30 ° C. The reaction time is usually from 1 to 24 hours, preferably from 2 to 5 hours. After the reaction is completed, the The reaction target compound (XX VI) can be collected from the reaction mixture according to a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding ethyl acetate to a water-insoluble organic solvent, and washing with water, separating an organic layer containing the target compound ' It is obtained by drying with anhydrous sulphuric acid, and then distilling off the solvent. -60-200413400 The compound obtained can be used according to the normal method if necessary. For example, recrystallization, silica gel chromatography, etc. (Project B b 5) This project is a process for deprotecting the protecting group of compound (XXVI) to produce compound (XXVII). (B a 6 Project) The reaction is carried out to achieve the conditions. (B B 6 Project) This project is a process for manufacturing the intermediate trichloroacetimidate body (XXVIII), which can be based on the above (B A 7 Project) _ ((2-3)) c method This method is a method for producing an intermediate (XXXI) used for the compound (I) in which R5 is a hydrogen atom or a halogen atom. (Project B c 1 Project) This project is The process of producing the compound (XXIX) by converting the 6-hydroxy group of the compound (XXV) obtained in the above (the processes of B b 1 to B b 3) to a halogen atom or a hydrogen atom. The process is to make the compound (XXIX) where R5e is a halogen atom, and it can be carried out according to the following methods ①, ② or ③. ① When 115 (: is a fluorine atom, this project can make the compound (XXV) in an inert solvent ) And a fluorinating agent. The solvent used is, for example, dichloromethane Halogenated hydrocarbons such as chlorotrichloromethane -61-200413400 •, ethers such as diethyl ether, 1,2-dimethoxyethane, preferably dichloromethane. The fluorinating agent used is, for example, diethylamine trifluoride Sulfur (DAST) The reaction temperature is usually -78C ~ 25C, preferably ~ 25. The reaction time is usually 1 ~ 18 hours, preferably 1 ~ 5 hours. ② When R5e is a chlorine atom or a bromine atom Occasion This project can be achieved by reacting the compound (XXV) with phosphorus trichloride, phosphorus tribromide, phosphine trichloride, phosphine tribromide, sulfenyl chloride or sulfenyl bromide in an inert solvent. The solvent used is preferably dichloromethane, chloroform, carbon tetrachloride and other halogenated hydrocarbons. 0 The reaction temperature is usually -50 ° c ~ 5 ° C, preferably -1 (rc ~ 30t: 〇 Reaction time is usually It is 1 to 18 hours, preferably 1 to 5 hours. ③ When R 5e is an iodine atom, this project can be achieved by reacting the compound (XXV) with iodine and triphenylphosphine in an inert solvent. The solvent used for the reaction is only required It does not affect the reaction, but it is not specific if it can dissolve the raw materials, for example, aliphatic hydrocarbons such as hexane, heptane, petroleum spirit; aromatic hydrocarbons such as benzene, toluene, xylene; methylene chloride, chloroform, and tetrachloride Carbon, dichloroethane, chlorobenzene and other halogenated hydrocarbons; ethyl acetate, propyl acetate, diethyl carbonate and other esters; ether, diisopropyl ether, tetrahydrofuran, dioxane and other ethers; methanol, ethanol, etc. Alcohols; methylamine, N, N-dimethylformamide, N, N-dimethylacetamide, and other amines, preferably ethers. The reaction temperature is usually a 50 ~ 100 ° C It should be 0t ~ 30 ° C. -62-200413400 The reaction time is usually 1 ~ 18 hours, preferably 1 ~ 5 hours. After the reaction is finished The target compound (XXIX) of the reaction can be collected from the reaction mixture according to a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding ethyl acetate insoluble in an organic solvent, washing with water, and separating the organic layer containing the target compound, After drying with anhydrous magnesium sulfate, etc., it is obtained by distilling off the solvent. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, etc. as required. (Project B c 1-2) In this project, when the compound ( XXIX) R5. When it is a hydrogen atom, it can be carried out by reacting the compound in which R is a bromine atom in the above (the BC 1-1 project) ② with tetrabutyltin hydride or lithium aluminum hydride in an inert solvent. The solvents used are, for example, aliphatic hydrocarbons such as hexane, heptane, petroleum spirit; aromatic hydrocarbons such as benzene, toluene, xylene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, etc., preferably Ethers.

反應温度通常爲一50°c〜50°c下進行，宜爲一 l〇°c〜30°C 〇反應時間通常爲1 0分〜1 6小時，宜爲1〜8小時。籲反應終了後，本反應目的化合物（XXIX )可依常法自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第B c 2工程） -63 - 200413400 本工程爲令化合物（XXIX) 1位保護基予以脫保護，而製造化合物（XXX )之工程，可依上述（第B a6工程）之條件進行反應而達成。 (第B c 3工程）本工程爲製造中間體三氯乙醯亞胺酸酯體（XXXI)之工程，可依上述（第B a 7工程）之條件進行反應而達成。 (2 — 4 ) d 法本方法爲含R 4a爲雙鍵，參鍵之中間體（XXII)，（ XXVIII)或（XXXI)之另一製造工程。 φ (第B d 1工程）本工程爲令化合物（XXXII) 1位烯丙基予以異構化之工程，可依上述（第B a 4①工程）之條件進行反應而達成。 (第B d 2工程）本工程爲令化合物（XXXIII) 3位羥基予以烷基化之工程，可依上述（第A a 1①工程）之條件進行反應而達成。 (第B d 3工程）本工程爲令化合物（XXXIV) 2位疊氮予以還原，轉換鲁爲胺後保護之工程。 ①胺合成反應本工程可於惰性溶劑中，與還原劑作用而達成。所使用溶劑爲例如，乙醚，四氫呋喃等醚類，宜爲四氫咲喃。所使用還原劑爲例如，氫化鋰鋁，硼氫化鈉等金屬氫化物類等，宜爲氫化鋰鋁。 -64 - 200413400 反應温度通常爲一5〇°c〜locrc下進行，宜爲〇°c〜50°c。反應時間通常爲0 . 5〜2 4小時，宜爲1〜5小時。反應終了後，本反應目的化合物可依常法，自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等而精製。 ②保護化反應本工程可依上述（第B a 2②工程）之條件進行反應而達成。 (第B d 4工程）本工程爲令化合物（XXXV ) 4位及6位羥基之保護基以酸處理而脫保護之工程，可依上述（第A a 5工程）之條件進行反應而達成，宜使用對甲苯磺酸來進行。 (第B d 5工程）本工程爲令化合物（XXXVI) 6位羥基予以保護之工程，可依上述（第B a 4②工程）之條件進行反應而達成。使用本工程所得化合物（XIX )，依第B a 5工程後述方法進行，可得中間體（XXII)。 (第B d 6工程）本工程爲令化合物（XXXVI) 6位羥基予以保護之工程，可依上述（第B b 1工程）之條件進行反應而達成。使用本工程所得化合物（XXIII)，依第B b 2工程後述 200413400 方法進行，可得中間體（xxviii)或（χχχι)。 (3 ) C 法 (第C a 1工程）本工程爲令化合物（ΧΧΠ) ，（XXVIII)或（XXXI)，與上述化合物（XI )進行葡糖基化反應，而製造化合物（ XXXVII )之工程。本工程可於惰性溶劑中，於觸媒存在下進行。所使用溶劑爲例如，二氯甲烷，氯仿等鹵化烴類。所使用觸媒爲例如四氯化錫，三氟硼烷/醚，氯化鋁，氯化亞鐵，三氟甲磺酸三甲矽烷酯，三氟甲磺酸銀等路易士酸；分子篩（4 A )。反應温度通常爲一50t〜40°C。反應時間通常爲1小時〜24小時，宜爲4小時。反應終了後，本反應目的化合物可依常法，自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層’以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第C a 2工程）本工程爲令二糖化合物（XXXVII)之胺基保護基予以脫保護’再將所得胺基與羧酸，其醯鹵或其酐以醯胺化，而製造化合物（XXXVIII)之工程。本工程之脫保護可令化合物（XXXVII )，於惰性溶劑中，與脫保護劑反應而達成 200413400 ，本工程之羧酸縮合反應可在惰性溶劑中，於鹼存在下，與縮合劑反應而達成，本工程之醯鹵反應可在惰性溶劑中，於鹼存在下，進行反應而達成。脫保護中所用溶劑爲例如，乙醚，四氫呋喃等醚類；乙酸；或其混合溶劑。所用脫保護劑爲鋅-乙酸。脫保護時反應温度通常爲〇°C〜100°c。脫保護時反應時間通常爲6分〜24小時，宜爲3小時。與羧酸之縮合反應所用縮合劑爲例如，DCC，WSC I等碳化二亞胺。與醯鹵之醯胺生成反應所用鹼爲例如，碳酸鈉，碳酸鉀，碳酸鋰等鹼金屬碳酸鹽類；碳酸氫鈉，碳酸氫鉀，碳酸氫鋰等鹼金屬碳酸氫鹽類；吡啶，二甲胺毗啶，三乙胺等有機驗。縮合反應所用溶劑爲例如，二氯甲烷，氯仿，四氯化碳，二氯乙烷，氯苯，二氯苯等鹵化烴類；乙醚，二異丙醚，四氫呋喃，二噚烷，二甲氧乙烷，二乙二醇二甲醚等醚類；乙腈，異丁腈等腈類；甲醯胺，N，N —二甲基甲醯胺，N，N —二甲基乙醯胺，N —甲基一 2 —毗咯酮，N — 甲基吡咯啶酮，六甲磷醯三胺等醯胺類；水及其混合溶劑〇縮合反應時反應時間通常爲〇°C〜100°c。縮合反應時反應温度通常爲6分〜24小時。 (第C a 3工程） -67 - 200413400 本工程爲令二糖化合物（XXXVIII)正位異構物之保護基予以脫保護，而製造化合物（XXXIX )之工程，係於惰性溶劑中，與酸觸媒反應而達成。所用溶劑爲例如，二氯甲烷，氯仿，四氯化碳，二氯乙烷，氯苯，二氯苯等鹵化烴類；乙腈，異丁腈等腈類。所用酸觸媒爲例如48 %氟化氫水溶液。反應温度通常爲0°C〜loot，宜爲室温。反應時間通常爲6分〜24小時，宜爲1 6小時。 (第C a 4工程）本工程爲令化合物（XXXIX)之正位異構物作成亞磷酸酯，再氧化，以製造磷酸酯（XL )之工程，可依第B a 5 之方法來進行。 (第C a 5工程）本工程爲令化合物（XL)保護基脫保護以製造化合物（ XLI)之工程’可依文獻（例如，τ· W. Greene, Protective Groups in Organic Synthesis)記載之方法，或依下方法而達成。當化合物（XLI )有數種保護基存在時，可以保護基對應方法組合依次進行。 ①當保護基爲芳院基之場合當保護基爲芳烷基時，可在惰性溶劑中，於觸媒存在下 ’在氫氣下水解而脫保護。所使用溶劑爲例如，四氫呋喃，二曙烷，乙醚等醚類；乙酸乙酯等酯類；甲醇，乙醇等醇類；甲酸，乙酸等有機酸類，宜爲乙醇。 -68 - 200413400 所使用觸媒爲例如，Pd-C ’氫氧化鈀，氫氧化鈀碳，鈀黑，宜爲氫氧化紀碳。反應温度通常爲0°C〜50°C，宜爲15°c〜25°c。反應時間通常爲1〜48小時，宜爲3〜24小時。反應終了後，本反應目的化合物（I )可依常法自反應混合物收集。例如，將反應混合物濾除觸媒，對所得濾液濃縮而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 · ② 當保護基爲苯基之場合當保護基爲苯基時，可於惰性溶劑中，在觸媒存在下，以接觸還原來脫保護。所使用溶劑爲例如，四氫呋喃，二噚烷，乙醚等醚類；乙酸乙酯等酯類；甲醇，乙醇等醇類；甲酸，乙酸等有機酸類，宜爲四氫呋喃。所使用觸媒宜爲氧化鉑。反應温度通常爲0°C〜50°C，宜爲15°C〜25°C。籲反應時間通常爲1〜4 8小時，宜爲1〜2 4小時。反應終了後，本反應目的化合物（I )可依常法自反應混合物收集。例如，將反應混合物濾除觸媒，對所得濾液濃縮而得。所彳守化合物視需要可依常法，例如，再結晶，纖維素層析等精製。 ③ 當保護基爲燒丙基之場合 -69 - 200413400 當保護基爲烯丙基之場合，可於惰性溶劑中，於絶觸媒下，將甲酸一三乙胺混合物於乙酸-三乙胺或鉻觸媒下，於95%乙醇水中回流，而將化合物（XL)烯丙基脫保護。所得化合物視需要可依常法，例如，再結晶，纖維素層析等精製。 (第C b 1工程）本工程爲令化合物（XXII) ，（XXVIII)或（ΧΧΧΙ), 與上述化合物（XIV )予以葡糖基化反應，而製造化合物 (XLII )之工程，可依第c a 1工程之條件進行反應而達成。 (第C b 2工程）本工程爲令二糖化合物（XLII)之胺基保護基予以脫保護，將所得胺基與羧酸，其醯鹵或其酐縮合，而製造化合物（XLIII )之工程，可依第C a 2工程之條件進行反應而達成。 (第C b 3工程）本工程爲令化合物（XL)之保護基予以脫保護，而製造化合物（XLI )之工程，可依第C a 5工程之條件進行反應而達成。 (第C b 4工程）本工程爲化合物（XLIII)中R4a爲下式 OR4b H2Cvs^/\r4c (式中，R 4b及R 4e之定義如上。）所表之基，將基R 4b -70 - 200413400 予以脫離之工程。本工程可於惰性溶劑中，與2，3 -二環一5，6—二氰基一1，4—苯醌（]〇]3(3)反應而達成。所使用溶劑爲例如，二氯甲烷等鹵化烴。反應温度通常爲室温〜50 °C。反應時間通常爲5分〜2 4小時。反應終了後，本發明目的化合物（XLIIIb )可依常法自反應混合物收集。例如，將反應混合物以惰性溶劑稀釋，以鹼性水溶液及水洗浄，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第C c 1工程）本工程爲令化合物（XXII) ，（XXVIII)或（XXXI)，與上述化合物（XIa)以葡糖基化反應，而製造化合物（ XXXVila)之工程。本工程可於惰性溶劑中，於觸媒存在下進行。本工程可依第C a 1工程之條件進行反應而達成〇 (第C c 2工程）本工程爲令二糖化合物（XXXVIIa)之胺基保護基予以脫保護，再將所得胺基與羧酸，其醯鹵或其酐進行醯胺化，而製造化合物（XXXIX )之工程。本工程可依第C a 2 工程之條件進行反應而達成。所得化合物（XXXIX )可依第C a 4工程及第C a 5工程，而得目的化合物（XLI)。 (4 ) D 法 -71 - 200413400 (第D a 1工程）本工彳壬爲令化合物（χ Π )之1級經基轉換成溴原子，而製造化合物（XLV )之工程，可於惰性溶劑中，與四溴化碳一三苯膦反應而達成。所使用溶劑爲例如，二氯甲烷，氯仿等鹵化烴類；四氫呋喃等醚類；苯等芳香族烴等。反應温度通常爲〇°C〜溶劑加熱回流温度，宜爲室温。反應時間通常爲6分〜1 6小時，宜爲1小時〜3小時。反應終了後，本反應目的化合物可依常法，自反應混合物收集。例如，將反應混合物中和後，濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第D a 2工程）本工程爲令化合物（XLV)溴原子與亞磷酸三烯丙酯反應，而製造磷酸二烯丙酯（XLVI)之工程，通常於無溶劑下進行。反應温度通常爲150 °C〜200 °C。 (第D a 3工程）本工程爲令化合物（XLVI)之4位及6位羥基之保護基予以脫保護，而製造二醇（XLVII )之工程，可於惰性溶劑中，與酸反應而達成。所使用溶劑爲例如，甲醇，乙醇等醇類；乙酸水溶液（ -72 - 200413400 例如，80%乙酸水溶液）等。所使用酸爲例如，乙酸，對甲苯磺酸等有機酸；氯化氫等無機酸。反應温度通常爲5 0 °C〜8 0 °C。反應時間通常爲1小時〜6小時。 (第D b 1工程）本工程爲令化合物（XXII) ，（XXVIII)或（XXXI)，與上述化合物（XLVII)以葡糖基化反應，而製造化合物（ XLVIII)之工程，可依第C a 1工程之條件進行反應而達 _ 成。 (第D b 2工程）本工程爲令二糖化合物（XLVIII)之胺基保護基予以脫保護，再將所得胺基與羧酸，其醯鹵或其酐縮合，而製造化合物（XLIX )之工程，可依第C a 2工程之條件進行反應而達成。 (第D b 3工程）本工程爲令化合物（XLIX)之保護基予以脫保護，而製 ® 造化合物（L )之工程，可依第C a 5工程之條件進行反應而達成。 (5 ) E 法 (弟E a 1工程）本工程爲令已知化合物（LIII )除去4個乙醯基，再於4 位及6位羥基架以亞異丙基，而得化合物（LIV )之工程，可依第A c 3工程之條件進行反應而達成。。 -73 - 200413400 (第E a 2工程）本工程爲令化合物（LI V )之2個羥基予以烷基化，而得化合物（LV )之工程，可依第A C 2工程之條件進行反應而達成。。 (第E a 3工程）本工程爲令化合物（LV)之烯丙基雙鍵予以氧化切斷爲醛後，還原，而製造化化合物（LVI )之工程，可依第A b 1工程之條件進行反應而達成。 (第E a 4工程）本工程爲令化合物（LVI)與膦反應，而製造磷酸酯（ LVIII)之工程，可依第Ab2工程之條件進行反應而達成〇 (第E a 5工程）本工程爲令化合物（LVIII )中4位及6位羥基之保護基予以脫保護，而製造二醇（LIX )之工程，可依第D a 3工程之條件進行反應而達成。 (第E b 1工程）本工程爲令化合物（XXII) ，（XXVIII)或（XXXI)，與上述化合物（LIX)進行葡糖基化反應，而製造化合物（ LX )之工程，可依第C a 1工程之條件進行反應而達成。 (第E b 2工程）本工程爲令二糖化合物（LX)之胺基保護基予以脫保護，再將所得胺基與羧酸，其醯鹵或其酐縮合，而製造化合物（LXI )之工程，可依第C a 2工程之條件進行反應而達 -74 - 200413400 成。 (第E b 3工程）本工程爲令化合物（LXI)之保護基予以脫保護，而製造化合物（LXII )之工程，可依第C a 5工程之條件進行。 (6 ) F 法 (第F a 1工程）本工程爲令已知化合物（LXIII)之4個苄基除去，再於 4位及6位羥基架以亞異丙基，而得化合物（LXIV )之工程，苄基之除去工程通常爲加水反應而達成，亞異丙基架橋工程可依第A a 3工程之條件進行反應而達成。 (第F a 2工程）本工程爲令（a)化合物（LXIV)之2個羥基予以烷基化， (b)將呋喃環氧化開裂，（c)將生成之羧基予以酯化而得化合物（LXV )之工程。 (a) 烷化工程可依第A c 2工程之條件進行反應而達成。 (b) 呋喃環氧化開裂工程可於惰性溶劑中，將呋喃化合物與過碘酸鈉反應而達成。所使用溶劑爲二氯甲烷，氯仿，四氯化碳等鹵化烴類；乙腈等腈類；水；及其混合溶劑，宜爲四氯化碳，乙腈及水混合溶劑。反應温度通常爲〇°C〜100°c，宜爲40°c〜80。(：。反應時間通常爲2小時〜20小時，宜爲1 〇小時〜1 5小時。 (c) 酯化工程可依常法達成。例如甲酯化之場合，可於惰 -75 - 200413400 性溶劑中，將羧酸化合物與重氮甲烷或三甲矽烷重氮甲院反應而達成。所使用溶劑爲如醚，四氫呋喃等醚類。反應温度通常爲o°c〜室温。 (第F a 3工程）本工程爲令化合物（LXV )之酯基還原，而得化合物（ LX VI )之工程。本工程可在惰性溶劑下，與還原劑反應而達成。所使用溶劑爲例如，甲醇，乙醇等醇類；及乙醚，四氫呋喃等醚類。所使用還原劑爲例如，氫化鋰鋁，硼氫化鈉等金屬氫化物，宜爲氫化鋰鋁。反應温度通常爲0 °C〜5 0 °C，宜爲室温。反應時間通常爲6分〜24小時。反應終了後，本反應目的化合物（LXVI )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層’以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第F a 4工程）本工程爲令化合物（LX VI)與膦反應，而製造磷酸二烯丙酯（LXVIII)之工程，可依第a b 2工程之方法進行反應而達成。 -76 - 200413400 (第F a 5工程）本工程爲令化合物（LXVIII)之4位及6位羥基保護基予以脫保護，而製造二醇（LXIXa )之工程，可依第D a 3 工程之方法進行反應而達成。 (第F b 1工程）本工程爲令化合物（XXII) ，（XXVIII)或（XXXI)，與上述化合物（LXIX)進行葡糖基化反應，而製造化合物 (LXX )之工程，可依第C a 1工程之方法進行反應而達成〇 (第F b 2工程）本工程爲令糖化合物（LXX)之胺基保護基予以脫保護，再將所得胺基與羧酸，其醯鹵或其酐縮合，而製造化合物（LXXI )之工程，可依第C a 2工程之條件進行反應而達成。 (第F b 3工程）本工程爲令化合物（LXXI)之保護基予以脫保護，而製造化合物（LXXII )之工程，可依第C a 5工程之條件進行反應而達成。 (G法） (第G a 1工程）本工程爲令化合物（VI)之烯丙基由硼氫化轉換爲3 -羥丙基，而製造化合物（LXXIII )之工程。本工程可在惰性溶劑下，與硼化合物以加成反應，再於鹼性水溶液中，與過氧化氫反應而達成。 -77 - 200413400 加成反應所使用溶劑爲例如，乙醚，四氫呋喃等醚類，氧化脫離反應所使用溶劑爲例如，氫氧化鈉水溶液，氫氧化鉀水溶液等鹼水溶液。所使用硼化合物爲例如，硼烷，9 一 B B N等。加成反應之反應温度通常爲0°C〜50°C，宜爲0°C〜室温，氧化脫離反應之反應温度通常爲〇它〜5 0 °C，宜爲0 °C〜室温。加成反應之反應時間通常爲6分〜4 8小時，氧化脫離反應之反應時間通常爲6分〜24小時。反應終了後，本反應目的化合物（LXXIII )可依常法自反應混合物收集。例如，將反應混合物濃縮，加入乙酸乙酯之不溶於水之有機溶劑，水洗後，分離含目的化合物之有機層，以無水硫酸鎂等乾燥後，蒸除溶劑而得。所得化合物視需要可依常法，例如，再結晶，矽膠層析等精製。 (第G a 2工程）本工程爲令化合物（LXXIII)變換成亞磷酸酯，再氧化，而製造化合物（LXXIV )之工程，可依第Ab2工程之條件進行反應而達成。 (第G a 3工程）本工程爲令化合物（LXXIV )之4位及6位羥基架橋之亞異丙基予以脫保護，而製造化合物（LXXV)之工程，可依第A a 5工程之條件進行反應而達成。 (第G b 1工程） -78 - 200413400 本工程爲令化合物（XXII) ，（XXVIII)或（XXXI)，與上述化合物（LXXV )進行葡糖基化反應，而製造化合物 (LXXVI )之工程，可依第c a 1工程之條件進行反應而達成。 (第G b 2工程）本工程爲令二糖化合物（LXXVI)之胺基保護基予以脫保護，再將所得胺基與羧酸，其醯鹵或其酐縮合，而製造化合物（LXXVII )之工程，可依第C a 2工程之條件進行反應而達成。 (第G b 3工程）本工程爲令化合物（LXXVII)之保護基予以脫保護，而製造化合物（LXX VIII )之工程，可依第C a 5工程之條件進行反應而達成。 (Η法） (第H a 1工程）本工程爲令化合物（V )烯丙基雙鍵予以氧化切斷作成醛後，還原，而製造化合物（Xlla )之工程，可依第Abl工程之條件進行反應而達成。 (第H a 2工程）本工程爲令化合物（Xlla )之1級羥基轉換爲溴原子，再與亞磷酸三烯丙酯反應，而製造磷酸二烯丙酯（XIII a) 之工程，可依第D a 1工程及第D a 2工程之條件進行反應而達成。 (第H a 3工程） -79 - 200413400 本工程爲令化合物（Xllla )二級羥基予以醯基化，而製造化合物（XIVa )之工程，可依第a a 8工程之條件進行反應而達成。本發明化合物（I )之投予形態爲例如，錠劑，膠囊劑 ’顆粒劑，散劑或糖漿劑等經口投予，或注射劑或栓劑等非經口投予等。此製劑可使用賦形劑，結合劑，崩散劑，滑劑，安定劑，矯味劑等添加劑，以習知方法來製造。使用量可視症狀，年齢等而異，一般成人每日爲0· 01 〜10m g/kg體重，1日以1回或數回來投予。 _ 以下，實施例及試驗例可詳細説明本發明，但本發明並不僅限於此。〔實施例1〕鱗酸基 6 - Ο—〔2—去氧—4— Ο—膦酸基—3 — Ο—〔 (R) — 3 —甲氧癸基〕一6— 0 —甲基一 2—〔（Z) — 11 — (十八碳燦釀基）胺基〕一 β - D-卩比喃葡糖基〕一 3— Ο-癸基—2—0— [(R) — 3 —羥基十四基]一 a— D —吡喃葡糖苷 · (1) 1’ 2: 5，6 - 一 — Ο —亞異丙基一3 — Ο —癸基一 α—D —呋喃葡萄糖（第A a 1工程）將1，2: 5，6—二—Ο-亞異丙基—α—D —呋喃葡萄糖 (17.0g，65.3 1mmol )及 1—(甲磺醯氧基）癸烷（15.34g， 64.90mmol)溶在DMF ( 65mL)，於冰冷卻下加入氫化鈉 (55%油中，3.4〇11^，77.92111111〇1)。於〇°C 下攪拌 15 分再於室温攪拌過夜。將反應液於冰冷卻下加入甲醇以分解氫 -80 - 200413400 化鈉，以乙酸乙酯稀釋。以水及飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮，進行矽膠層析純化。溶離以環己烷 —乙酸乙酯（9 : 1，再以4 : 1 )，可得油狀標題化合物（ 22.5g，產率 98%)。 IR vmax(Il) 2987, 2928, 2857 cm'1. 400 MHz ιϋ NMR (CDC13) δ 0.88 (3H, t, J = 6.6 Hz)? 1.27 (14H, bs), 1.32 (3H? s), 1.36 (3H, s), 1.43 (3H, s), 1.50 (3H，s)，1.55 - 1.5 8 (2H，m), 3.52 (1H, m)，3.59 (1H, m), 3.86 (1H, d, J = 3.7Hz), 3.99 (1H, dd, J = 5.9, 8.8 Hz), 4.08 (1H, d, J = 5.9 Hz), 4.11 (1H, t, J = 6.6 Hz), 4.14 (1H, m), 4.31 (1H, m), 4.53 (1H, d, J = 4.4 Hz), 5.88 (1H, d, J = 4.4 Hz). (2) 烯丙基 3 - O—癸基一 α一 d—吡喃葡糖苷（第A a 2工程）將（1 )所得化合物（20.6g)加入含2%鹽酸之烯丙醇（ 3 0 0 mL)，回流15分。將反應液濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（1 : i，再以1 : 3 )，可得油狀標題化合物（l4.6g，產率98%, a，b-混合物）。其可使用於下一反應。 (3) 烯丙基 3 - Ο—癸基一 4，6— 0 —亞異丙基一 α，β —D—吡喃葡糖苷（第A a 3工程）將（2 )所得化合物（1.2〇g，3.33mmol )溶於D M F ( 2.5mL·)，加入 2,2-二甲氧丙烷（2.5mL)及 p_Ts〇H ( 50mg) ’於室温下攪拌6小時。反應液以乙酸乙酯稀釋，以重碳 -81 - 200413400 酸鈉溶液，飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮，進行矽膠層析純化。溶離以環己院一乙酸乙酯（3 :1 )，可得油狀標題化合物之α體（9 0 2 m g，產率6 8 % )及β體 ( 293 mg，產率 22%)。 α體： 400 MHz lH NMR (CDC13) δ 〇.88 (3H? t? J = 6.6 Hz), 1.26 (14H，bs)，1·41 (3H，s)，1·49 (3H，s)，1.53- 1.60 (2H，m), 2.27 (1H, d，J = 7.3 Hz，OH)，3.46-3.86 (8H, m)，4.04 (1H, m)，4.21 (1H，m)，4·92 (1H，d，j = 3.7 Hz)，5.22-5.35 (2H, m), 5.93 (1H, m). β體： 400 MHz 'H NMR (CDC13) δ 〇.88 (3H, t) J = 6.6 Hz), 1.26 (14H，bs)，1·41 (3H，s)，1.49 (3h，s)，1.55- 1.60 (2H, m)， 2.29 (1H, d，J = 2.2 Hz，OH), 3·25 (1H，m), 3.31 (1H，t， J = 8.8 Hz)，3·45 (1H，m), 3.59-3.67 (2H，m)，3.75-3.82 (2H， m)，3.91 (1H，dd，J = 5.1，11.0 Hz)，4.14 (1H, dd，J = 6.2， 12·8 Hz), 4·35 (1H，dd，J = 5.1，12.5 Hz), 4.40 (1H，d, J = 8.1 Hz), 4.92 (1H, d, J = 3.7 Hz), 5.20-5.35 (2H, m), 5.93 (1H, m) · (4)烯丙基 2 — O— [(R) 一 3—(第三丁二甲Ϊ夕院氧基）十四基]—3 - Ο —癸基—4，6— Ο —亞異丙基一 α— D — 吡喃葡糖苷（第A a 4工程）將（3)所得 α 體（4.58g，i145inm〇l)及（R) - 3—（第三丁二甲矽烷氧基）一1〜（甲磺醯氧基）十四烷（4.84g， -82 - 200413400 1 1 ·45ιηιηο1 )溶在DMF ( 3mL)，加入氫化鈉（5 5 %油中， 1.50g, 34.38mmol)。於室温下攪拌過夜，再於5 0 t下攪拌 2小時’於冰冷卻下加入甲醇以分解氫化鈉，以乙酸乙酯稀釋。將溶液以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷-乙酸乙酯 (9:1)，可得油狀標題化合物（5.60g，產率67%)。 400 MHz NMR (CDC13) δ 0.04 (6H, s), 0.878 (9H, s), 0.88 (6H，t, J = 6.6 Hz)，1.26 ( 3 2 H，b s)，1. 3 9 -1 · 5 9 (1 OH，m, 含 3H, s at d 1.41 ppm and 3 H，s at d 1.48 ppm), 1.67-1.77 (2H，m)，3.29 (1H, dd, J = 3.7, 8.8 Hz), 3.45-3.85 ( 1 0H, m), 4.04 (1H，dd，J = 6.6，12.5 Hz), 4.18 (1H, dd, J = 5.1, 12.5 Hz), 4.92 (1H, d, J = 3.7 Hz), 5.20-5.34 (2H, m), 5.92 (1H, m). FABMS (陽離子）m/z，727 [M + H] + · (5)烯丙基 2 — O— [(R) — 3—羥基十四基]一 3— O 一癸基一 α - D-吡喃葡糖苷（第A 35工程）將（4)所得化合物（ 500mg，0.688mmol)溶在甲醇（ 10mL)，加入對甲苯磺酸（24mg)，於室温下攪拌40分，減壓濃縮後以乙酸乙酯稀釋。將溶液以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（1 : 1 )，可得標題化合物（217mg，產率58% )。 IR vmax(KBr) 3 3 5 8 (寬），3270 (寬），292 1，2850，1 466 cm·1· 400 MHz !H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 200413400 (32H，bs)，1.40- 1.73 (6H, m), 1.93 (1H, t, J = 6.5 Hz, OH), 2.44 (1H，d，J = 2.2 Hz，OH)，2;93 (1H，bs，OH)，3.30 (1H, dd, J = 3.7, 9.5 Hz), 3.50- 3.92 ( 1 0H, m), 4.05 (1H, m), 4.20 (1H, m), 5.01 (1H, d, J = 3.7 Hz), 5.22-5.34 (2H, m), 5.95 (1H，m)· FABMS (陽離子）m/z，57 3 [M + H] +，595 [M + Na] + . HRFABMS，C33H6407Na 計算値：595.4550 〇實測値： 595.454 1. (6) (E)— 1—丙烯基 2— O - [(R)— 3 —羥基十四基]—3— O—癸基—a— D-吡喃葡糖苷（第A a 6工程）將（5)所得化合物（210mg，0.367mmol)溶在四氫呋喃 (THF，4mL)，加入氫活化之 Ir[C8H12(MePh2P)2]PF6 ( 5mg)，於室温攪拌過夜後濃縮，可得標題化合物（ 21〇mg，定量的）。其可使用於下一反應。 400 MHz !H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (32H, bs), 1.41-1.73 (9H, m), 1.87 (1H, br, OH), 2.47 (1H, br, OH), 2.74 (1H, bs, OH), 3.32 (1H, m), 3.54-3.92 ( 10H, m), 5·17 (1H，d，J = 3.7 Hz)，5.20 (1H，m)，6.19 (1H，J = 1.5’ 2.5 Hz). FABMS (陽離子）m/z，57 3 [M + H] +，595 [M + Na] + · (7) (E) — 1 一丙嫌基 6 —〇一第三丁二甲石夕院基一 3 —Ο —癸基—2— Ο— [(R) — 3 —經基十四基]—α—D — [I比喃葡糖苷（第A a7工程）將（6)所得化合物（200mg，0.349mmol)溶在二氯甲院 200413400 (4 m L )，力Π入第三丁二甲石夕院氯（58mg，0.384mmol)及 DMAP ( 47mg，〇.3 8 4mmol)，於室温攪拌過夜後，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（4 : 1 )混合溶液，可得油狀標題化合物（217mg,產率90% )。 IR vmax(膜）3456 (寬），2926，2855，1465 cm-1· 400 MHz ]H NMR (CDC13) δ 0.08 (6H, s), 0.88 (6H, t, J = 6.6 Hz)，0.90 (9H，s)，1.26 (32H，bs)，1.40- 1.75 (9H, m，含 3H, d, J = 7.3 Hz at 1.55 ppm), 2.75 (1H, bs? OH), 2.84 (1H, bs, OH), 3.30 (1H, m), 3.53-3.87 ( 10H, m), 5.14 (1H, · d, J = 2.9 Hz), 5.20 (1H, m6.20 (1H, d, J=12.5 Hz). FABMS (陽離子）m/z，687 [M + H] + , 709 [M + Na]' HRFABMS C39H78〇7SiNa 計算値：709.54 14。實測値： 709.5393. (8) (E)— 1—丙烯基 4 —〇一烯丙氧羰基一 2— 0—[ (R) — 3—(烯丙氧羰氧基）十四基]一 6 —〇一（第三丁二甲矽烷基）一 3— 0 —癸基—α — D—吡喃葡糖苷（第A a 8工程） _ 將（7)所得化合物（203mg，0.293mmol)溶在甲苯（ 6 m L )，加入卩比U定（〇 . 5 0 g，6 · 3 2 m m ο 1 )，於冰冷卻下加入光氣（ 200mg，0.674mmol)，劇烈攪拌10分。加入條丙醇 (0.60g, 10.331mmol)，於冰冷卻下攪拌1小時。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗，於硫酸鎂下乾燥。過濾濃縮後，以矽膠柱層析純化。溶離以環己烷-乙酸乙酯（1 4 : 1 )，可得標題化合物及不明物混合物（ -85 - 200413400 3 2 5mg )。其可使用於下一反應。 (9) (E) — 1 一丙烯基 4 一〇—烯丙氧羰基一 2— 〇—[ (R) — 3—（烯丙氧羰氧基）十四基]_3— Ο—癸基—α — D—吡喃葡糖苷（第A a9工程）將（8)所得混合物（ 325mg)溶在二氯甲烷（2.5mL) 及乙腈（5.0mL)，加入矽膠粉（10〇11^)及48%氫氟酸水溶液（100mg)，於室温攪拌30分後，以二氯甲烷稀釋。以重碳酸鈉溶液及食鹽水洗，於硫酸鎂下乾燥。過濾濃縮後以矽膠柱層析純化。溶離以環己烷-乙酸乙酯（2 : 1 )，可得標題化合物（126mg，2工程產率58% )。 IR vmax(膜）3527 (寬），2926，2855，1 747，1 678 (w) cm·1. 400 MHz lH NMR (CDC13) δ 0.86-0.90 (6H, m), 1.26 (32H, bs), 1.50- 1.68 (7H, m), 1 · 8 8 -1 · 9 2 (2 H，m)，2 · 3 4 (1H，bs, OH)，3·37 (1H，m)，3.57-3.78 (8H，m), 4.60-4.80 (6H，m)， 5.13-5.40 (6H，m)，5.90-5.95 (2H，m), 6.16 (1H，qd，J=i.5， 12.5 Hz). FABMS (HHi ) m/z9 763 [M + Na] + . HRFABMS iNa 計算値：763.4973。實測値： 7 63.4962. (10) ( E ) 一 1—丙燃基 2 - 0— [(R) — 3-（稀丙氧鑛氧基）十四基]—6—0—〔2 —去氧一 4一0—二烯丙膦酸基一 3— Ο—〔（R) — 3 —甲氧癸基〕一 6— Ο —甲基一 2 一〔（三氯乙氧羰基）胺基〕一 β— D—吡喃葡糖基〕一 3 — 〇 —癸基一 α—D—吡喃葡糖苷（第C a 1工程） -86 - 200413400 將三氯甲基亞胺醯基2—去氧一 4一 0-二烯丙膦酸基一 3 —0—〔（R) —3 —甲氧癸基〕一6— 0— 甲基—α，β— D — 吡喃葡糖苷（180mg，0.2 13mmol)及（9)所得化合物（ 158mg，0.187 mmol)溶在二氯甲烷（5 mL)，加入分子篩4 A ( 400mg ) ，AgOTf ( 1 OOmg，0.389mmol )及 TMSOTf ( 10mg, 0.045mmol )，於氮氣及室温下攬拌6小時。反應液以二氯甲烷稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（2 : 1 )，可得膠狀之標題化合物（ 283mg，產率 93% )。 IR vmax(膜）3400-3080, 2926，2855，1744 cm]· 400 MHz lU NMR (CDC13) δ 0.88 (9H, t, J = 6.6 Hz), 1.25 (44H，bs)，1.40- 1.77 (9H, m，含 3H，dd，J=1.5，6.6 Hz at 1.55 ppm), 1.87- 1.89 (2H，m)，3.24 (1H，m)，3·28 (3H，s)， 3.32 (1H，dd，J 二 3.7，9.5 Hz), 3.39 (3H, s)，3.4 0 - 3 · 8 0 (1 4 H， m), 4.05 (1H, d，J=1 1.7 Hz), 4.26 (1H, m), 4.50-4.88 ( 1 2H, m), 5.12 (1H，d, J = 2.9 H z ), 5 . 1 6 (1 H，d d，J = 6.6，12.5 Hz), 5.70 (1H, brosd), 5.21-5.46 (8H, m), 5.70 (1H, m), 5.89-5.98 (4H, m), 6.16 (1H, qd, J = 1.5, 12.5 Hz), 6.68 (1H,寬， NH). FABMS (陽離子）m/z，1442 [M + Na，35C1] +，1444. HRFABMS C68H 1 1 7 3 5 C13N021P 計算値·· 1442.68 1 9。實測値：1442.6820. (11) (E) — 1—丙嫌基 4一 O—燦丙氧類基一 2 - Ο — -87 - 200413400 「（R) — 3—（嫌丙氧羯氧基）十四基」—3— 0 —癸基〜 6— Ο—〔2 —去氧—4 一 0 — 一燒丙鱗酸基一 3—0—〔（R) 一 3 一甲氧癸基〕一6— 0—甲基一2—〔（Ζ) — 11—(十八碳燒醯基）胺基〕一 β - D-卩比喃葡糖基〕一 -卩比喃葡糖苷（第C a2工程）將（10)所得化合物（95 2mg，O.6 6 9mmol)溶在乾燥 THF ( 21mL)，加入乙酸（14mL)及金屬鋅（800mg)，劇烈攪拌3小時。將反應液過濾濃縮，以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，將所得一級胺溶在T H F ( 4mL )。加入含重碳酸鈉（l〇〇mg )之水（0.9mL )及1 1 —十八烯酸之醯氯（ 227mg, 0.803mmol)之 T H F ( 4mL )溶液，於室温劇烈攪拌2小時。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（3 : 2)，可得膠狀之標題化合物（439mg，產率43% )及構造不明物（260mg )° IR vmax(膜）3 308 (w), 3086 (w)，2926，285 6，1 748, 1 677, 1 6 6 0 cm'1. 400 MHz !H NMR (CDC13) δ 0.86-0.90 ( 12H, m), 1.25 (62H, bs), 1.40- 1.80 (1 3H，m，含 3 H，d d，J = 1 . 5，6 · 6 H z a t 1.54 ppm), 1.82- 1.89 (2H, m), 1.98-2.02 (4H, m), 2.22-2.26 (2H, m)，3.22-3 ·79 (20H，m，含 3 H，s，at 3 · 2 8 p p m，an d 3 H，s，at 3.37 ppm), 3.84 (1H, m), 4.04 (1H, m), 4.23 (1H, m), 4.53- -88 - 200413400 4.87 (12H? m), 5.03-5.3 8 ( 1 2H, m)? 5.88-5.97 (4H, m), 6.05 (1H, m), 6.13 (1H, qd, J=1.5, 12.5 Hz). FABMS (陽離子）m/z，1 532 [M + Na] + · HRFABMS CnHMsNOnPNa 計算値：1 5 3 3.0230。實測値： 1533.0239. (12) 4— 0—_ 丙氧羯基一2 — Ο—〔（R) — 3—（烯丙氧羰氧基）十四基〕一 3-0—癸基一 6—0—〔2 —去氧一 4一 Ο—二烯丙膦酸基一 3 — 0—〔（R) — 3 —甲氧癸基〕—6— Ο —甲基一 2—〔（Z) — 11-（十八碳烯醯基）胺基〕一 β— D—吡喃葡糖基〕一 α—D —吡喃葡糖苷（第C a 3工程）將（1 1 )所得化合物（410mg，0.288mmol )溶在二氯甲烷（7.7mL)—乙腈（16.8mL)，加入48%氫氟酸（ 5.25mL)，於室温下攪拌過夜。反應液以乙酸乙酯稀釋，以重..碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷-乙酸乙酯（1 :1再以1 : 3 )，可得膠狀之標題化合物（300mg，產率 75% )。 IR vmax(膜）3297 (w)，3086 (w)，2927，285 6，1 748，1 65 2， 1 550，1464 cm'1. 400 MHz lH NMR (CDC13) δ 0.86-0.89 ( 1 2H, m), 1.25 (62H, bs)，1.40- 1.90 ( 1 3H，m，含 OH), 1.92-2.02 (4H，m)，2.17-2.23 (2H，m)，3 · 1 0-3.7 4 (2 OH，m，含 3 H，s，at 3 . 1 7 pp m，a n d 3H, s, at 3.37 ppm), 3.88-4.70 ( 14H, m), 4.81 (1H, m), 200413400 5.18-5.42 (11H? m), 5.89-6.00 (4H, m), 6.09 (1H, d, J = 7.3 Hz, NH). FABMS (陽離子）m/z，1492 [M + Nal] + . HRFABMS, C8〇H144N02〇PNa 計算値：1 4 9 · 9 9 1 7。實測値： 149.9875. (13) 二烯丙膦酸基 4— Ο —烯丙氧羰基一 2— 0—「 (R) — 3—（烯丙氧羰氧基）十四基」一 3 - Ο—癸基一 6 一 Ο—〔2 —去氧—4— Ο —二烯丙膦酸基一 3— 0—〔（R) —3 —甲氧癸基〕一6— 0 —甲基一2—〔（Z) — 11一（十八碳烯醯基）胺基〕一 β— D-吡喃葡糖基〕一 α - D-吡喃葡糖苷（α體）及二烯丙膦酸基 4 一 Ο-烯丙氧羰基一 2 — Ο—「（R) — 3—(烯丙氧羰氧基）十四基」一3 - 0—癸基—6 — Ο-〔2 -去氧一 4— 0 —二烯丙膦酸基—3 - 0-〔 (R) — 3 —甲氧癸基〕一6 — 0 —甲基一2 —〔（Ζ) — 11 一（十八碳烯醯基）胺基〕一 β - D —吡喃葡糖基〕一 β— D 一吡喃葡糖苷（β體）（第Ca4工程） (a )將（12)所得化合物（ 300mg，0.199mmol)溶在二氯甲烷（12mL)，加入 Na2S04 ( 630mg ) ，1H-四唑（ 460mg，6.57mmol)及二異丙胺基磷酸二嫌丙酯（510mg， 2.08mmol)，於氮氣及室温下攪拌3 0分，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（1 : 1 )，可得油狀二烯丙膦酸基 4一 Ο—烯丙氧羰基一 2— 0—「（R) — 3-（烯丙氧羰氧基）十四基」—3— Ο -癸基一 6 — 0—〔2-去氧 —4— 0 —二嫌丙膦酸基一3 - 0—〔（R) — 3 —甲氧癸基〕 -90 - 200413400 —6— 0 —甲基一 2 —〔（Ζ) - 11一（十八碳烯醯基）胺基〕一 β— D—吡喃葡糖基〕一 D—吡喃葡糖苷（268mg,產率 8 1 % )。其可用於下一反應。 (b )將（a )所得化合物（ 256mg，0.17mmol)溶在 THF ( 25mL)，加入 3 0 % Η 2 Ο 2 ( 5 0 0 mg )，於冰冷卻下攪拌30分，以乙酸乙酯稀釋。以丨〇%硫代硫酸水及食鹽水洗，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（1 : 1再以〇 : 1 )，可得油狀標題化合物β體（122mg，產率47%)及α體（99mg,產率籲 3 8% )。 β體： IR vmax(膜）3310 (w)，3086 (w)，2926，2856, 1748，1 677, 1551, 1 4 6 3 cm"1. 400 MHz lH NMR (CDC13) δ 0.80- 1.90 ( 1 2H, m), 1.26 (62H, bs), 1.40-1.75 (10H, m), 1.80-1.90 (2H, m), 1.99-2.05 (4H, m), 2.20-2.22 (2H, m), 3.20 (1H, m), 3.27 (3H? s), 3.33 (1H, m), 3.38 (3H, m), 3.40-3.80 ( 14H, m), 3.99 (1H, m), 籲 4.25 (1H, m), 4.49 (1H, t, J = 9.5 Hz), 4.55-4.61 (11H, m), 4.70 (1H, d, J = 8.8 Hz), 4.77 (1H, m), 4.93 (1H, m), 5.23-5.43 (14H, m), 5.86-5.98 (6H, m), 7.49 (1H, d, J = 10.3 Hz, NH). FABMS(陽離子）m/z，1 652 [M + Na] + · HRFABMS，C86Hi53N023P2Na 計算値：1 6 5 3.0 2 0 7 〇實測値：1653.0219. -91 - 200413400 α體·· IR vma“膜）3 303 (w)，308 6 (w)，2926，2856，1 747，1 654， 1 546，1464 cm-1. 400 MHz lR NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.25 (62H, bs)，1.39- 1.74 ( 10H，m), 1.83- 1.88 (2H, m), 1.99-2.02 (4H, m), 2.21-2.25 (2H, m), 3.23 (1H, m), 3.27 (3H, s), 3.33 (1H, m), 3.38 (3H, m), 3.48-3.77 ( 1 2H, m), 3.83 (1H, dd, J = 8.8，9.5 Hz)，3.96 (1H，m)，4,01 (1H，m), 4.25 (1H，dd，J = 9.5, 18.3 Hz), 4.54-4.61 (1 2 H，m)，4.6 2 - 4.7 3 (2H, m), 4.76-4.80 ( 1H, m), 5.22-5.41 (14H, m), 5.71 (1H, dd, J = 2.9, 6.6 Hz), 5.88-6.01 (6H, m), 6.51 (1H, d, J = 8.1 Hz, NH). FABMS(陽離子）m/z，1 652 [M + Na] + · HRFABMS， C86H153N023P2Na 計算値：1 6 5 3.0 2 0 7 。實 S!l 値：1653.0184. (14)膦酸基 6-0—〔2 —去氧一 4— Ο —膦酸基—3 — 〇 —〔（R) — 3 一甲氧癸基〕一6— Ο —甲基一 2 —〔（Ζ) 一 11 一（十八碳烯醯基）胺基〕一 β - D —吡喃葡糖基〕一 3 一 0-癸基一 2—0— [(R) — 3_經基十四基]一 a— D — 0比喃葡糖苷（第C a5工程）將（13)所得 α 體（90mg，0.055mmol)溶在無水 THF ( 6mL )，力口入 PPh3 ( 15mg，0.057mmol ) ，Et3N ( 60mg， 0.593mmol) ，HCOOH ( 5 1 mg，1.108mmol )及 Pd(PPh3)4 ( 1 5 mg，0.01 3 mmol )，於氮氣及55 °C下攪拌20小時。反應 -92 - 200413400 終了後’過濾濃縮，以D E A E -纖維素8 g之柱精製。溶離以 CHCl3-Me0H-H20 (2:3:1)之 0.05mol/L AcO_NH4 溶液可得含目的物之部份。收集部份與CHCl3-Me0H-H20 (1:1:1) 之混合物，力□入CHC13及0.15mol/L鹽酸水，於分液漏斗中攪拌，收集下層CHC13層並濃縮可得蠟狀之標題化合物 (5 3 m g ,產率 74%)。 IR vmax(KBr) 329 1 (w), 3076 (w), 2925, 2853, 1 628, 1 554, 14 6 6 cm"1. 400 MHz lH NMR ( C D C13 - C D 3 O D , 5:1) δ 0.86-0.90 (12H, m), 1.27 (62H, bs)? 1.40- 1.75 ( 1 2H, m), 1.99-2.03 (4H, m), 2.20-2.26 (2H，m)，3.23-4.1 2 (26H，m，含 2 個 3H, s at 3.30 and 3.40 ppm), 4.76 (1H, d, J = 8.1 Hz), 5.3 3-5.39 (2H, m), 5.7 1 (1H, dd, J = 3.3, 7.0 Hz). FABMS (陰離子）m/z，1 300 [Μ-ΗΓ，1 322 [M + Na-2H]' HRFABMS，C66H128N〇i9P2 計算値·· 1 3 00 · 8 5 5 6。實測値·· 1300.8560. C66H129N019P2 分析計算値：C，60.85; Η, 9.98; N，1.08; P， 4.76。實測値：C，60.41; H，10.17; N，1·09; P，4.54. 〔實施例2〕膦酸基 6— Ο—〔2-去氧一4— Ο-膦酸基一 3— Ο—〔 (R) 一 3 —甲氧癸基〕一6— 0 —甲基一 2 —〔 ( Z) 一 11一 (十八碳烯醯基）胺基〕一 β— D -吡喃葡糖基〕一 3 - Ο — 癸基一 2 — 0— [(R) - 3 -羥基十四基]一 β— D—吡喃葡糖苷（第C a 5工程） -93 - 200413400 將實施例1 ( 13)所得β體（I12mg,0.069mmol)，依實施例1 ( 14)之方法反應，可得蠟狀之標題化合物（72mg, 產率8 0 % )。 IR vmax(KBr) 3 286 (w), 3073 (w), 2925, 2854, 1 628, 1 556, 14 6 6 cm'1. 400 MHz lU NMR (C D C13 - C D 3 0 D , 5:1) δ 0.86-0.90 ( 12H, m), 1·27 (62H, bs)，1.40- 1.80 ( 1 2H，m)，2.00-2.08 (4H，m)， 2·24-2·28 (2H，m)，3.1 3-4.06 (26H，m,含 2 個 3H，s at 3.30 and 3.40 ppm), 4 · 9 2 - 4 · 9 7 ( 2 H，m)，5 · 3 4 - 5 · 3 8 (2 H，m) · FABMS (陰離子），m/z，1 300 [M-H]·· C66H129N019P2 分析計算値：c，60.85; H，9.98; N，1.08; P， 4 · 7 6。實測値：C，6 0 · 3 6 ; H，1 0.1 7 ; N，1 · 1 2 ; P，4 · 6 8 . 〔實施例3〕鱗酸基 3 — O —癸基—6— 0-〔2 —去氧—4— O —鱗酸基一3 — Ο 一〔 ( R ) — 3 一甲氧癸基〕一6 — Ο 一甲基一2 — 〔（Ζ ) - 11一（十八碳烯醯基）胺基〕一 β— D—毗喃葡糖基〕一 2— 0—十四基一 α— D—吡喃葡糖苷 (1)燃丙基 3— 0 —癸基一 4’ 6 - 0—亞異丙基—2— 0 一十四基—a— D—吡喃葡糖苷（第A a4工程）將實施例 1 ( 3 )所得 β 體（5.15g，12.86m m 〇1 )及 1 —( 甲磺醯氧基）十四烷（4.51g，15.43mmol )溶在DMF ( 25mL )溶液，加入氫化鈉（55%油中，67〇11^，15.43111111〇1)。依實施例1 ( 4)之方法處理，可得油狀標題化合物（7.02g, 產率9 2 % )。 -94 - 200413400 400 MHz !H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (36H，bs), 1.40 (3H，s)，1.47 (3H, s)，1.50- 1.60 (4H，m)， 3.10-4.35 (12H, m)，4.37 (1H，d，J = 8.1 Hz), 5.17-5.34 (2H， m), 5.91 (1H，m)· (2) 烯丙基 3 - O —癸基—2 — O—十四基—β— D —吡喃葡糖苷（第A a5工程）將（1 )所得化合物（7 · 0 2 g , 1 1 · 7 6 m m ο 1 )，依實施例1 (5 )之方法反應，可得標題化合物（5.〇2g，產率77% ) 400 MHz !H NMR (CDC13) δ 0.88 (6Η? t, J = 6.6 Hz), 1.26 (36H, bs), 1.52- 1.62 (4H, m), 2.07 (1H, t, J = 6.6 Hz, OH), 2.46 (1H? d, J 二 2.2 Hz，OH), 3 . 1 0 - 4 · 2 2 (1 2 H，m), 4 · 3 8 (1 H， d, J = 8.1 Hz), 5.21-5.35 (2H, m), 5.92 (1H, m). (3) (E) — 1—丙烯基 3— O —癸基一 2— O —十四基一 β - D-吡喃葡糖苷（第A a6工程）將（2 )所得化合物（2.5 1 g , 4 · 5 1 m m ο 1 )，依實施例1 ( 6)之方法反應，可得標題化合物（2.05g，產率82%)。籲 400 MHz NMR (CDC13) δ 0.88 (6Η, t, J = 6.6-7.3 Hz), 1.26(36H, bs), 1.53- 1.60 (7H, m，含 3H，dd, J = 1.5, 7.3 Hz, at 1.56 ppm), 2.06 (1H, t, J = 6.6 Hz, OH), 2.44 (1H, d, J=1.5 Hz, OH), 3.14-3.92 (10H, m), 4.52 (1H, d, J = 7.3 Hz), 5.12 (1H, m), 6.21 (1 H , q d，J = 1 · 5，12.5 Hz). (4) (E)— 1—丙烯基 3— O —癸基一 2— O —十四基一 β - D-吡喃葡糖苷（第A a7工程） -95 - 200413400 將（3 )所得化合物（2.45 g, 0 ·4.10m mol )，依實施例1 (7 )之方法反應，可得油狀標題化合物（2.80g,產率 89% )。 400 MHz NMR (CDC13) δ 0.08 (6H, s), 0.86-0.90 ( 1 5H, f m，含 9H，s，at 0·89 ppm)，1.26 (36H，bs)，1.53- 1.60 (7H， m), 3.02 (1H, d, J = 2.2 Hz, OH), 3.13-3.24 (2H, m), 3.33 (1H, m), 3.49-3.89 (7H, m), 4.47 (1H, d, J = 7.3 Hz), 5.11 (1H, m), 6.20 (1H, dd，J = 1.7，12.1 Hz). (5) (E)— 1 —丙烯基 4 一〇一烯丙氧羰基一 6 — ◦一 (第三丁二甲矽烷基）一3— Ο—癸基一 2— 〇—十四基一 β 一 D-吡喃葡糖苷（第A a8工程）將（4 )所得化合物（2.80g，4· 17mmol )，依實施例1 ( 8)之方法反應，可得標題化合物（2.99g，產率95%)。 400 MHz ]H NMR (CDC13) δ 0.03 (6H, s), 0.86-0.89 ( 1 5H, m，含 9H，s, at 0.87 ppm)，1.25 (3 6H，bs)，1·5 卜 1.56 (7H, m), 3.22 (1H, dd, J = 7.8, 9.9 Hz), 3.35 (1 H，d d，J = 8.8，9 · 9 Hz), 3.43 (1H, m), 3 · 5 2 - 3 · 8 1 ( 6 H , m)，4 · 4 5 (1 H, d，J = 7 · 8 Hz), 4.60-4.72 (3H, m), 5.11 (1H, m), 5.27 (1H, d, J = 10.7 Hz), 5.36 (1H, d, J=18.5 Hz), 5.93 (1H, m), 6.21 (1H, m). (6) (E) — 1 一丙烯基 4 —〇一烯丙氧羰基一 3 — 0 — 癸基—2 — Ο-十四基一 β— D-卩比喃葡糖苷（弟A a 9工程 ) 將（5 )所得化合物（2· 98g，3.95 mmol )，依實施例1 ( 9 )之方法反應，可得標題化合物（2 · 1 6 g，產率8 5 % )。 -96 - 200413400 IR Vmax(膜）3453 (寬），2925, 2854，1 757，1681 cm·1· 400 MHz NMR (CDC13) δ 0.86 (6H, t，J = 6.6 Hz)，1·26 (36H，bs)，1.50- 1.60 (7H，m)，2.20 (1H，dd，J = 5.8, 8.0 Hz), 3.24 (1H, m)，3.40 (1H, dd, J = 8.8, 9.5 Hz), 3.45 (1H，m)， 3.54-3.68 (3H, m), 3.72-3.82 (3H, m), 4.51 (1H, d, J = 8.1 Hz), 4.64-4.72 (3H, m), 5.12 (1H, m), 5.29 (1H, d, J=10.3 Hz), 5.37 (1H, d, 18.3 Hz), 5.93 (1H, m), 6.21 (1H, qd, J=1.5, 12.5 Hz). FABMS (陽離子）m/z，663 [M + Na] + · HRFABMS C37H6 8 0 8 Na 計算値：663.48 1 2。實測値： 663.4802. (7) (E) - 1 一丙燃基 6 — Ο—〔2 —去氧—4一 Ο— 二烯丙膦酸基一3— 0—〔（R) — 3—甲氧癸基〕一 6— 0 —甲基一 2-〔（三氯乙氧羰基）胺基〕—β - D-吡喃葡糖基〕一 3— 〇 —癸基一 2— Ο—十四基一β— D—毗喃葡糖苷（第C a 1工程）將（6 )所得化合物（3 4 7 m g，0 · 5 4 1 m m ο 1 )，依實施例1 (10)之方法反應，可得標題化合物（577mg，產率89%) 〇 IR vmax(膜）3 3 60-3 1 90 (寬），2926，285 6，1754，1 7 3 6，1680 (w) cm"1. 400 MHz lU NMR (CDC13) δ 0.88 (9H, t, J = 6.6 Hz), 1.25 (48H，bs)，1.43- 1.76 (9H，m，含 3H, dd，J=1.5，7.3 Hz，at 1.62 ppm)，3.21 (1H，m)，3·27 (3H，s)，3·32 (1H，m)，3.38 -97 - 200413400 (3H, s)5 3.40-3.64 (9H, m), 3.70-3.79 (6H, m)? 3.90 (1H? m), 4.32 (1H, m), 4.48 (1H, d, J = 7.3 Hz), 4.55-4.66 (9H, m), 4.84 (1H, m), 5.11-5.40 (6H, m), 5.87-5.98 (3H, m), 6·32 (1H，m)，6.62 (1H，bs, NH). FABMS (陽離子）m/z，1 342 [M + Na, 35C1] +，1 344· HRFABMS 計算値：C64H113Cl3N018PNa 計算値：1 342.6666 。實測値：1 3 4 2 · 6 6 8 7 . (8) (E) —1 一丙燃基 4— Ο—條丙氧羰基—2— Ο — 「（R) — 3—（烯丙氧羰氧基）十四基」—3— Ο-癸基— 6— 0—〔2 —去氧一 4— 0 —二烯丙膦酸基—3— 0—〔（R) —3 —甲氧癸基〕一 6— 0 —甲基一2—〔（Z) — 11—(十八碳烯醯基）胺基〕一 β - D-吡喃葡糖基〕—β— D—吡喃葡糖苷（第C a2工程）將（7 )所得化合物（4 0 5 m g，0 · 3 0 6 m m ο 1 )，依實施例1 (11)之方法反應，可得標題化合物（302 mg，產率70% )° IR vmax(膜）3292 (w)，2926，2855，1 755，1 678，1 652，1 5 52, 1465 cnT1· 400 MHz lU NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.20-1·74 (79H，m，含 3H，d, J = 7.4 Hz, at 1.56 ppm)，2.0 卜2.26 (6H，m)，3.16-3.32 (7H，m，含 3H, s，at 3·27 ppm)，3·37 (3H， s), 3.50-3.80 ( 1 2H，m)，3.92 (1H，m)，4·04 (1H，t，J = 9.5 Hz)，4.12 (1H，m), 4·26 (1H，m)，4·44 (1H，d，J = 8.1 Hz)， 4.53-4.61 (4H, m), 4.62-4.66 (2H, m), 4.89 (1H, d, J = 8.1 -98 - 200413400The reaction temperature is usually from -50 ° C to 50 ° C, preferably from 10 ° C to 30 ° C. The reaction time is usually from 10 minutes to 16 hours, and preferably from 1 to 8 hours. After the completion of the reaction, the target compound (XXIX) of the reaction can be collected from the reaction mixture according to a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding ethyl acetate, an insoluble organic solvent, washing with water, separating the organic layer containing the desired compound, drying over anhydrous magnesium sulfate, and then distilling off the solvent. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project B c 2) -63-200413400 This project is to deprotect the protecting group of compound (XXIX) at the 1st position, and the process of producing compound (XXX) can be carried out by reacting according to the conditions of the above (Project B a6) Reached. (Project B c 3) This project is a process for manufacturing the intermediate trichloroacetamidate body (XXXI), which can be achieved by performing the reaction according to the conditions of the above (Project B a 7). (2-4) d method This method is another manufacturing process containing intermediates (XXII), (XXVIII) or (XXXI) containing R 4a as a double bond. φ (Project B d 1) This project is a process for isomerizing the allyl group of compound (XXXII), and can be achieved by performing the reaction according to the conditions described above (Project B a 4①). (Project B d 2) This project is a process for alkylating the hydroxyl group at the 3-position of compound (XXXIII), and it can be achieved by performing the reaction according to the conditions described above (Project A a 1①). (Project B d 3) This project is to reduce the azide at the 2-position of compound (XXXIV) and convert it to amine for protection. ① Amine synthesis reaction This project can be achieved by reacting with a reducing agent in an inert solvent. The solvent used is, for example, ethers such as diethyl ether, tetrahydrofuran, etc., and tetrahydrofuran is preferred. The reducing agent used is, for example, metal hydrides such as lithium aluminum hydride, sodium borohydride, etc., and lithium aluminum hydride is preferred. -64-200413400 The reaction temperature is usually -50 ° c ~ locrc, preferably 0 ° c ~ 50 ° c. The response time is usually 0. 5 to 24 hours, preferably 1 to 5 hours. After completion of the reaction, the target compound of the present reaction can be collected from the reaction mixture by a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding an ethyl acetate-insoluble organic solvent, washing with water, separating the organic layer containing the target compound, drying over anhydrous magnesium sulfate, and evaporating the solvent. The obtained compound can be purified by a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. ②Protection reaction This project can be achieved by reacting according to the conditions of the above (Article B a 2② Project). (Project B d 4) This project is a process for deprotecting the protective groups of the hydroxyl groups at the 4- and 6-positions of the compound (XXXV) by acid treatment, and can be achieved by performing the reaction according to the conditions described above (Project A a 5). It is preferred to use p-toluenesulfonic acid. (Project B d 5) This project is a project for protecting the hydroxyl group at the 6-position of the compound (XXXVI). It can be achieved by performing the reaction according to the conditions described above (Project B a 4②). Using the compound (XIX) obtained in this project, the intermediate (XXII) can be obtained according to the method described later in Project B a 5. (Project B d 6) This project is a project for protecting the hydroxyl group at the 6-position of the compound (XXXVI). It can be achieved by performing the reaction according to the conditions described above (Project B b 1). Using the compound (XXIII) obtained in this project, according to the method of 200413400 described later in the Bb 2 project, an intermediate (xxviii) or (χχχι) can be obtained. (3) Method C (C a 1 Project) This project is a process for making a compound (XXX), (XXVIII) or (XXXI) and a glucosylation reaction with the above compound (XI) to produce a compound (XXXVII) . This project can be carried out in an inert solvent in the presence of a catalyst. The solvents used are, for example, halogenated hydrocarbons such as dichloromethane and chloroform. The catalysts used are, for example, tin tetrachloride, trifluoroborane / ether, aluminum chloride, ferrous chloride, trimethylsilyl trifluoromethanesulfonate, and Lewis acid such as silver trifluoromethanesulfonate; molecular sieves (4 A). The reaction temperature is usually -50t ~ 40 ° C. The reaction time is usually 1 hour to 24 hours, preferably 4 hours. After completion of the reaction, the target compound of the present reaction can be collected from the reaction mixture by a conventional method. For example, the reaction mixture is neutralized, concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project C a 2) This project is to deprotect the amine protecting group of the disaccharide compound (XXXVII) ', and then the resulting amine group and carboxylic acid, its halogen halide or its anhydride are aminated with fluorene to produce a compound ( XXXVIII). The deprotection of the project can be achieved by reacting the compound (XXXVII) with a deprotecting agent in an inert solvent to achieve 200413400. The carboxylic acid condensation reaction of this project can be achieved by reacting with a condensing agent in an inert solvent in the presence of a base The halogenation reaction of this project can be achieved by performing the reaction in an inert solvent in the presence of a base. The solvent used in the deprotection is, for example, ethers such as diethyl ether, tetrahydrofuran, acetic acid, or a mixed solvent thereof. The deprotecting agent used was zinc-acetic acid. The reaction temperature during deprotection is usually 0 ° C ~ 100 ° c. The reaction time during deprotection is usually 6 minutes to 24 hours, preferably 3 hours. The condensing agent used in the condensation reaction with a carboxylic acid is, for example, a carbodiimide such as DCC, WSC I. The bases used in the reaction with ammonium halides to form ammonium amines are, for example, alkali metal carbonates such as sodium carbonate, potassium carbonate, and lithium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, and lithium hydrogen carbonate; pyridine, di Organic tests such as methylamine pyridine and triethylamine. The solvents used in the condensation reaction are, for example, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene and other halogenated hydrocarbons; ether, diisopropyl ether, tetrahydrofuran, dioxane, and dimethoxy Ethers such as ethane, diethylene glycol dimethyl ether; nitriles such as acetonitrile, isobutyronitrile; formamidine, N, N-dimethylformamide, N, N-dimethylacetamide, N —Methyl-2—pyrrolidone, N—methylpyrrolidone, hexamethylphosphonium triamine, and other amines; water and its mixed solvent. 0 The reaction time during the condensation reaction is usually 0 ° C ~ 100 ° c. The reaction temperature during the condensation reaction is usually 6 minutes to 24 hours. (Project C a 3) -67-200413400 This project is to deprotect the protective group of the ortho isomer of disaccharide compound (XXXVIII), and the process of manufacturing compound (XXXIX) is in an inert solvent and acid A catalyst reaction was reached. The solvents used are, for example, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene; and nitriles such as acetonitrile and isobutyronitrile. The acid catalyst used is, for example, a 48% aqueous hydrogen fluoride solution. The reaction temperature is usually 0 ° C ~ loot, preferably room temperature. The reaction time is usually 6 minutes to 24 hours, preferably 16 hours. (Project C a 4) This project is a process of making the ortho isomer of compound (XXXIX) into a phosphite and reoxidizing it to produce phosphate (XL), which can be carried out according to the method of Section B a 5. (Project C a 5) This project is a process for deprotecting the protective group of compound (XL) to produce compound (XLI). 'According to the literature (for example, τ · W. Greene, Protective Groups in Organic Synthesis). When the compound (XLI) has several kinds of protecting groups, the corresponding methods of protecting groups can be performed in sequence. ① When the protecting group is an aromatic group When the protecting group is an aralkyl group, it can be deprotected by hydrolysis in hydrogen in an inert solvent in the presence of a catalyst. The solvents used are, for example, ethers such as tetrahydrofuran, dioxane, and ether; esters such as ethyl acetate; alcohols such as methanol and ethanol; organic acids such as formic acid and acetic acid, preferably ethanol. -68-200413400 The catalyst to be used is, for example, Pd-C 'palladium hydroxide, palladium hydroxide carbon, palladium black, preferably carbon hydroxide. The reaction temperature is usually 0 ° C ~ 50 ° C, preferably 15 ° c ~ 25 ° c. The reaction time is usually 1 to 48 hours, preferably 3 to 24 hours. After the reaction is completed, the target compound (I) of the present reaction can be collected from the reaction mixture by a conventional method. For example, the reaction mixture is filtered to remove the catalyst, and the obtained filtrate is concentrated. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. · ② When the protective group is phenyl group When the protective group is phenyl group, it can be deprotected by contact reduction in an inert solvent in the presence of a catalyst. The solvents used are, for example, ethers such as tetrahydrofuran, dioxane, and ether; esters such as ethyl acetate; alcohols such as methanol and ethanol; organic acids such as formic acid and acetic acid, preferably tetrahydrofuran. The catalyst used is preferably platinum oxide. The reaction temperature is usually 0 ° C ~ 50 ° C, preferably 15 ° C ~ 25 ° C. The reaction time is usually 1 to 48 hours, preferably 1 to 24 hours. After the reaction is completed, the target compound (I) of the present reaction can be collected from the reaction mixture by a conventional method. For example, the reaction mixture is filtered to remove the catalyst, and the obtained filtrate is concentrated. The compound to be held can be purified by a conventional method, for example, recrystallization, cellulose decantation, etc., if necessary. ③ When the protective group is propyl group -69-200413400 When the protective group is allyl group, it can be mixed with acetic acid-triethylamine or acetic acid-triethylamine in an inert solvent under an absolute catalyst. Under a chromium catalyst, the compound (XL) was deprotected by refluxing in 95% ethanol water. The obtained compound can be purified by a conventional method, for example, recrystallization, cellulose decantation, etc., if necessary. (Project C b 1) This project is to make the compound (XXII), (XXVIII) or (XXIX) and the above-mentioned compound (XIV) glucosylated, and the process of manufacturing compound (XLII) can be carried out according to Section ca 1Conditions of the project were reached by reaction. (Project C b 2) This project is a process for deprotecting the amine protecting group of a disaccharide compound (XLII), and condensing the obtained amine group with a carboxylic acid, its halogen, or its anhydride to produce a compound (XLIII) , Can be achieved according to the conditions of the C a 2 project. (Project C b 3) This project is to deprotect the protective group of compound (XL), and the process of manufacturing compound (XLI) can be achieved by reacting according to the conditions of project C a 5. (Project C b 4) In this project, R4a in compound (XLIII) is the following formula OR4b H2Cvs ^ / \ r4c (wherein R 4b and R 4e are as defined above.) -200413400 Works to be disengaged. This project can be accomplished by reacting with 2,3-bicyclo-5,6-dicyano-1,4-benzoquinone (] 〇] 3 (3) in an inert solvent. The solvent used is, for example, dichloride Halogenated hydrocarbons such as methane. The reaction temperature is usually room temperature to 50 ° C. The reaction time is usually 5 minutes to 24 hours. After the reaction is completed, the target compound (XLIIIb) of the present invention can be collected from the reaction mixture according to a conventional method. For example, the reaction The mixture is diluted with an inert solvent, washed with an alkaline aqueous solution and water, and dried with anhydrous magnesium sulfate, and then distilled off the solvent. The obtained compound can be purified according to a conventional method, for example, recrystallization, silica gel chromatography, etc. as required. C c 1 Project) This project is a process for making compound (XXII), (XXVIII) or (XXXI) and the above compound (XIa) by glucosylation reaction to produce compound (XXXVila). This project can be used in an inert solvent In the presence of a catalyst, this project can be achieved by performing the reaction according to the conditions of Project C a 1 (Project C c 2) This project is to deprotect the amino group of the disaccharide compound (XXXVIIa) , And then the resulting amine group and carboxylic acid, which The process of producing ammonium halides or its anhydride by amidation and producing compound (XXXIX). This project can be achieved by reaction according to the conditions of Project C a 2. The obtained compound (XXXIX) can be achieved according to Project C a 4 and Project C a 5 project, to obtain the target compound (XLI). (4) D method -71-200413400 (the D a 1 project) This work is to convert the first-grade compound (χ Π) into a bromine atom, and The process of producing compound (XLV) can be achieved by reacting with carbon tetrabromide-triphenylphosphine in an inert solvent. The solvents used are, for example, halogenated hydrocarbons such as methylene chloride, chloroform; ethers such as tetrahydrofuran; benzene, etc Aromatic hydrocarbons, etc. The reaction temperature is usually 0 ° C to the reflux temperature of the solvent, preferably room temperature. The reaction time is usually 6 minutes to 16 hours, preferably 1 hour to 3 hours. After the reaction is completed, the target compound of the reaction may be Collect the reaction mixture according to a conventional method. For example, after neutralizing the reaction mixture, concentrating, adding ethyl acetate insoluble organic solvent, washing with water, separating the organic layer containing the target compound, and drying with anhydrous magnesium sulfate, etc. , Distilled off the solvent The obtained compound can be purified according to ordinary methods, for example, recrystallization, silica gel chromatography, etc. as required. (Project D a 2) In this project, the bromine atom of the compound (XLV) is reacted with triallyl phosphite, and The process of manufacturing diallyl phosphate (XLVI) is usually carried out in the absence of a solvent. The reaction temperature is usually 150 ° C ~ 200 ° C. (Project D a 3) This project is to make the 4th and The protecting group of the hydroxyl group at the 6-position is deprotected, and the process of manufacturing a diol (XLVII) can be achieved by reacting with an acid in an inert solvent. The solvents used are, for example, alcohols such as methanol and ethanol; aqueous acetic acid (-72-200413400, for example, 80% aqueous acetic acid) and the like. The acids used are, for example, organic acids such as acetic acid, p-toluenesulfonic acid, and inorganic acids such as hydrogen chloride. The reaction temperature is usually 50 ° C to 80 ° C. The reaction time is usually 1 hour to 6 hours. (Project D b 1) This project is to make compound (XXII), (XXVIII) or (XXXI) react with the above-mentioned compound (XLVII) by glucosylation to produce compound (XLVIII). The conditions of a 1 project are reacted to achieve success. (Project D b 2) This project is to deprotect the amine protecting group of the disaccharide compound (XLVIII), and then condense the obtained amine group with a carboxylic acid, its halogen halide or its anhydride to produce a compound (XLIX). The project can be achieved by performing the reaction according to the conditions of the C a 2 project. (Project D b 3) This project is to deprotect the protective group of compound (XLIX), and the process of making compound (L) can be achieved by reacting according to the conditions of project C a 5. (5) Method E (E a 1 project) In this project, the known compound (LIII) is removed by 4 acetamidine groups, and then the 4- and 6-position hydroxyl groups are substituted with isopropylidene to obtain the compound (LIV). The project can be achieved by performing the reaction in accordance with the conditions of the A3 project. . -73-200413400 (Ea 2 project) This project is to alkylate 2 hydroxyl groups of compound (LI V), and to obtain compound (LV), it can be achieved by reaction according to the conditions of AC 2 project . . (Project E a 3) This project is the process of making the allyl double bond of compound (LV) oxidized and cut to aldehyde and then reducing it, and the process of manufacturing chemical compound (LVI) can be based on the conditions of project A b 1 Achieved by reaction. (Project E a 4) This project is to make the compound (LVI) react with phosphine, and the process of manufacturing phosphate ester (LVIII) can be achieved according to the conditions of Project Ab2. (Project E a 5 Project) This project In order to deprotect the protective groups of the hydroxyl groups at the 4- and 6-positions in the compound (LVIII), the process for producing a diol (LIX) can be achieved by performing a reaction according to the conditions of the D a 3 project. (Project E b 1) This project is to make compound (XXII), (XXVIII) or (XXXI) and glucosylation reaction with the above compound (LIX), and the process of manufacturing compound (LX) can be carried out according to Section C a 1 The conditions of the project are achieved by reaction. (Project E b 2) This project is to deprotect the amine protecting group of the disaccharide compound (LX), and then condense the obtained amine group with a carboxylic acid, its halogen halide or its anhydride to produce a compound (LXI). The project can be reacted according to the conditions of the C a 2 project to reach -74-200413400. (Project E b 3) This project is to deprotect the protective group of compound (LXI), and the process of manufacturing compound (LXII) can be carried out according to the conditions of project C a 5. (6) F method (the F a 1 project) This project is to remove the four benzyl groups of the known compound (LXIII), and then use isopropylidene at the 4 and 6 hydroxyl groups to obtain the compound (LXIV) Of the engineering, the removal of benzyl is usually achieved by adding water, and the isopropylidene bridge project can be achieved by performing the reaction according to the conditions of Section Aa3. (Project F a 2) This project is to alkylate two hydroxyl groups of (a) compound (LXIV), (b) oxidatively crack furan, and (c) esterify the resulting carboxyl group to obtain a compound ( LXV) project. (a) The alkylation process can be achieved by performing the reaction in accordance with the conditions of the A c 2 project. (b) Furan epoxidation cracking can be accomplished by reacting furan compounds with sodium periodate in an inert solvent. The solvents used are halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile; water; and a mixed solvent thereof, preferably a mixed solvent of carbon tetrachloride, acetonitrile, and water. The reaction temperature is usually 0 ° C ~ 100 ° c, preferably 40 ° c ~ 80. (: The reaction time is usually 2 hours to 20 hours, preferably 10 hours to 15 hours. (C) The esterification process can be achieved by conventional methods. For example, in the case of methylation, it can be inert -75-200413400. In the solvent, the carboxylic acid compound is reacted with diazomethane or trimethylsilazane. The solvents used are ethers such as ether, tetrahydrofuran, etc. The reaction temperature is usually o ° c ~ room temperature. (Section F a 3 Project ) This project is to reduce the ester group of compound (LXV) to obtain compound (LX VI). This project can be achieved by reacting with a reducing agent in an inert solvent. The solvents used are, for example, alcohols such as methanol and ethanol And ethers such as diethyl ether, tetrahydrofuran, etc. The reducing agent used is, for example, lithium aluminum hydride, sodium borohydride and other metal hydrides, preferably lithium aluminum hydride. The reaction temperature is usually 0 ° C ~ 50 ° C, preferably Room temperature. The reaction time is usually 6 minutes to 24 hours. After the reaction, the target compound (LXVI) of the reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is concentrated, and ethyl acetate is added to the water-insoluble organic solvent. , After washing, the organic layer containing the target compound is separated and dried with anhydrous magnesium sulfate, and then the solvent is distilled off. The obtained compound can be purified according to conventional methods, for example, recrystallization, silica gel chromatography, etc. as required. (Article F a 4 Project) This project is to make the compound (LX VI) react with phosphine, and the process of manufacturing diallyl phosphate (LXVIII) can be achieved by performing the reaction according to the method of the ab 2 project. -76-200413400 (the F a 5 Process) This process is to deprotect the hydroxyl groups at the 4- and 6-positions of the compound (LXVIII), and the process for manufacturing the diol (LXIXa) can be achieved by performing the reaction according to the method of the D a 3 project. (Section F Project b 1) This project is to make compound (XXII), (XXVIII) or (XXXI) and glucosylation reaction with the above compound (LXIX), and the process of manufacturing compound (LXX) can be carried out according to project C a 1 The method is carried out to achieve the reaction (the F b 2 project). This project is to deprotect the amino group protecting group of the sugar compound (LXX), and then condensing the resulting amino group with a carboxylic acid, its halogen, or its anhydride, and The manufacturing process of compound (LXXI) can be carried out according to Article C a 2 (The F b 3 project) This project is to deprotect the protective group of the compound (LXXI), and the process of manufacturing the compound (LXXII) can be reacted according to the conditions of the C a 5 project (Method G) (Project G a 1) This project is a process for converting the allyl group of compound (VI) from borohydride to 3-hydroxypropyl group, and producing compound (LXXIII). Addition reaction with boron compound under inert solvent, and reaction with hydrogen peroxide in alkaline aqueous solution. -77-200413400 The solvent used for the addition reaction is, for example, ethers such as diethyl ether and tetrahydrofuran, and the solvent used for the oxidation-desorption reaction is, for example, an aqueous solution of sodium hydroxide or an aqueous solution of potassium hydroxide. The boron compound used is, for example, borane, 9-B B N, and the like. The reaction temperature of the addition reaction is usually 0 ° C ~ 50 ° C, preferably 0 ° C ~ room temperature, and the reaction temperature of the oxidation and separation reaction is usually 0 ° ~ 50 ° C, preferably 0 ° C ~ room temperature. The reaction time of the addition reaction is usually 6 minutes to 48 hours, and the reaction time of the oxidation desorption reaction is usually 6 minutes to 24 hours. After completion of the reaction, the target compound (LXXIII) of the present reaction can be collected from the reaction mixture by a conventional method. For example, the reaction mixture is concentrated, and an ethyl acetate-insoluble organic solvent is added. After washing with water, the organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate, and the solvent is distilled off. The obtained compound may be purified according to a conventional method, for example, recrystallization, silica gel chromatography, and the like, if necessary. (Project G a 2) This project is to convert the compound (LXXIII) into a phosphite and re-oxidize it, and the process of manufacturing the compound (LXXIV) can be achieved by reacting according to the conditions of the Ab2 project. (Project G a 3) This project is to deprotect the isopropylidene at the 4- and 6-position hydroxyl bridge of compound (LXXIV), and the process of manufacturing compound (LXXV) can be based on the conditions of Project A a 5 Achieved by reaction. (Project G b 1) -78-200413400 This project is a process for producing compound (LXXVI) by subjecting compound (XXII), (XXVIII) or (XXXI) to a glucosylation reaction with the above compound (LXXV), It can be achieved according to the conditions of the first ca 1 project. (Project G b 2) This project is to deprotect the amine protecting group of the disaccharide compound (LXXVI), and then condensing the obtained amine group with a carboxylic acid, its halogen halide or its anhydride to produce a compound (LXXVII). The project can be achieved by performing the reaction according to the conditions of the C a 2 project. (Project G b 3) This project is to deprotect the protective group of compound (LXXVII), and the process of manufacturing compound (LXX VIII) can be achieved by performing the reaction according to the conditions of Project C a 5. (Method) (Project H a 1) This project is to make the compound (V) allyl double bond oxidized and cut to form aldehyde, and then reduce it. The process of manufacturing compound (Xlla) can be based on the conditions of the Abl project Achieved by reaction. (Project H a 2) This project is to convert the first hydroxyl group of compound (Xlla) to a bromine atom, and then react with triallyl phosphite to produce diallyl phosphate (XIII a). The conditions of Project D a 1 and Project D a 2 were achieved by reaction. (Project H a 3) -79-200413400 This project is to make the secondary hydroxyl group of compound (Xllla) fluorinated, and the process of producing compound (XIVa) can be achieved by performing the reaction according to the conditions of project a a 8. The administration form of the compound (I) of the present invention is, for example, oral administration such as troches, capsules, granules, powders or syrups, or parenteral administration such as injections or suppositories. This preparation can be manufactured by conventional methods using additives such as excipients, binding agents, disintegrating agents, lubricants, stabilizers, flavoring agents and the like. The amount used may vary depending on symptoms, age, etc. Generally, an adult will be administered from 0.01 to 10 mg / kg of body weight per day, and will be administered once or several times a day. _ Hereinafter, the present invention will be described in detail by examples and test examples, but the present invention is not limited thereto. [Example 1] Scale acid group 6-0-[2-deoxy-4-0-phosphonic acid group-3-0-[(R)-3-methoxydecyl]-6-0-methyl one 2 — [(Z) — 11 — (octadecyl group) amine group] —β-D-pyranoglucosyl] —3—O-decyl—2—0 — [(R) — 3 —Hydroxytetradecyl] —a—D—glucopyranoside · (1) 1 '2: 5,6-one — 0 —isopropylidene — 3 — 0 —decyl — α —D —furanose ( Project A a 1) Put 1,2: 5,6-di-2-O-isopropylidene-α-D-glucofuranose (17. 0g, 65. 3 1mmol) and 1- (methanesulfonyloxy) decane (15. 34g, 64. 90mmol) was dissolved in DMF (65mL), and sodium hydride (55% oil, 3. 4〇11 ^, 77. 92111111〇1). Stir for 15 minutes at 0 ° C and then overnight at room temperature. The reaction solution was added with methanol under ice cooling to decompose hydrogen -80-200413400 sodium chloride, and diluted with ethyl acetate. It was washed with water and saturated saline, dried over magnesium sulfate, filtered and concentrated, and then purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (9: 1, then 4: 1) to obtain the title compound (22. 5g, yield 98%). IR vmax (Il) 2987, 2928, 2857 cm'1. 400 MHz ιϋ NMR (CDC13) δ 0. 88 (3H, t, J = 6. 6 Hz)? 1. 27 (14H, bs), 1. 32 (3H? S), 1. 36 (3H, s), 1. 43 (3H, s), 1. 50 (3H, s), 1. 55-1. 5 8 (2H, m), 3. 52 (1H, m), 3. 59 (1H, m), 3. 86 (1H, d, J = 3. 7Hz), 3. 99 (1H, dd, J = 5. 9, 8. 8 Hz), 4. 08 (1H, d, J = 5. 9 Hz), 4. 11 (1H, t, J = 6. 6 Hz), 4. 14 (1H, m), 4. 31 (1H, m), 4. 53 (1H, d, J = 4. 4 Hz), 5. 88 (1H, d, J = 4. 4 Hz). (2) Allyl 3-O-decyl-α-d-glucopyranoside (Project A a 2) The compound obtained in (1) (20. 6g) Add allyl alcohol (300 mL) containing 2% hydrochloric acid and reflux for 15 minutes. The reaction solution was concentrated and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (1: i, then 1: 3) to give the title compound (l4. 6 g, yield 98%, a, b-mixture). It can be used in the next reaction. (3) Allyl 3-0-decyl-1,6-0-isopropylidene-1 α, β-D-glucopyranoside (Project A a 3) The obtained compound (2) (1. 20 g, 3. 33mmol) in D M F (2. 5mL ·), 2,2-dimethoxypropane (2. 5 mL) and p_TSOH (50 mg) 'were stirred at room temperature for 6 hours. The reaction solution was diluted with ethyl acetate, washed with a heavy carbon -81-200413400 sodium solution, saturated brine, dried over magnesium sulfate, filtered and concentrated, and purified by silica gel chromatography. After dissolving with ethyl acetate (3: 1) in cyclohexyl acetate, the α-form of the title compound (920 mg, yield 68%) and β-form (293 mg, yield 22%) were obtained. Alpha body: 400 MHz lH NMR (CDC13) δ 〇. 88 (3H? T? J = 6. 6 Hz), 1. 26 (14H, bs), 1.41 (3H, s), 1.49 (3H, s), 1. 53- 1. 60 (2H, m), 2. 27 (1H, d, J = 7. 3 Hz, OH), 3. 46-3. 86 (8H, m), 4. 04 (1H, m), 4. 21 (1H, m), 4.92 (1H, d, j = 3. 7 Hz), 5. 22-5. 35 (2H, m), 5. 93 (1H, m). β-body: 400 MHz 'H NMR (CDC13) δ 〇. 88 (3H, t) J = 6. 6 Hz), 1. 26 (14H, bs), 1.41 (3H, s), 1. 49 (3h, s), 1. 55- 1. 60 (2H, m), 2. 29 (1H, d, J = 2. 2 Hz, OH), 3.25 (1H, m), 3. 31 (1H, t, J = 8. 8 Hz), 3.45 (1H, m), 3. 59-3. 67 (2H, m), 3. 75-3. 82 (2H, m), 3. 91 (1H, dd, J = 5. 1, 11. 0 Hz), 4. 14 (1H, dd, J = 6. 2, 12 · 8 Hz), 4 · 35 (1H, dd, J = 5. 1, 12. 5 Hz), 4. 40 (1H, d, J = 8. 1 Hz), 4. 92 (1H, d, J = 3. 7 Hz), 5. 20-5. 35 (2H, m), 5. 93 (1H, m) · (4) allyl 2 — O— [(R) — 3 — (third butyl dimethyl oxenyloxy) tetradecyl] — 3-Ο — decyl — 4, 6-0-isopropylidene-α-D-glucopyranoside (Project A a 4) The α-body obtained in (3) (4. 58g, i145inmol) and (R)-3-(third butyl dimethylsilyloxy) 1 ~ (methanesulfonyloxy) tetradecane (4. 84g, -82-200413400 1 1 · 45ιηιο1) were dissolved in DMF (3mL), and sodium hydride (55% oil, 1. 50g, 34. 38mmol). It was stirred at room temperature overnight, and then stirred at 50 t for 2 hours'. Under ice cooling, methanol was added to decompose sodium hydride, and diluted with ethyl acetate. The solution was washed with water and saturated brine, and dried over magnesium sulfate. It was concentrated by filtration and purified by silica gel chromatography. Dissolve in cyclohexane-ethyl acetate (9: 1) to give the title compound (5. 60 g, yield 67%). 400 MHz NMR (CDC13) δ 0. 04 (6H, s), 0. 878 (9H, s), 0. 88 (6H, t, J = 6. 6 Hz), 1. 26 (3 2 H, b s), 1. 3 9 -1 · 5 9 (1 OH, m, including 3H, s at d 1. 41 ppm and 3 H, s at d 1. 48 ppm), 1. 67-1. 77 (2H, m), 3. 29 (1H, dd, J = 3. 7, 8. 8 Hz), 3. 45-3. 85 (1 0H, m), 4. 04 (1H, dd, J = 6. 6, 12. 5 Hz), 4. 18 (1H, dd, J = 5. 1, 12. 5 Hz), 4. 92 (1H, d, J = 3. 7 Hz), 5. 20-5. 34 (2H, m), 5. 92 (1H, m). FABMS (cation) m / z, 727 [M + H] + · (5) allyl 2 — O— [(R) — 3-hydroxytetradecyl] — 3 — O — decyl — α-D- Gluconoside (Project A 35) The compound obtained in (4) (500mg, 0. 688 mmol) was dissolved in methanol (10 mL), p-toluenesulfonic acid (24 mg) was added, and the mixture was stirred at room temperature for 40 minutes. The solution was washed with a sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. The solution was concentrated by filtration and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (1: 1) to obtain the title compound (217 mg, yield 58%). IR vmax (KBr) 3 3 5 8 (width), 3270 (width), 292 1, 2850, 1 466 cm · 1 · 400 MHz! H NMR (CDC13) δ 0. 88 (6H, t, J = 6. 6 Hz), 1. 26 200413400 (32H, bs), 1. 40- 1. 73 (6H, m), 1. 93 (1H, t, J = 6. 5 Hz, OH), 2. 44 (1H, d, J = 2. 2 Hz, OH), 2; 93 (1H, bs, OH), 3. 30 (1H, dd, J = 3. 7, 9. 5 Hz), 3. 50- 3. 92 (1 0H, m), 4. 05 (1H, m), 4. 20 (1H, m), 5. 01 (1H, d, J = 3. 7 Hz), 5. 22-5. 34 (2H, m), 5. 95 (1H, m) · FABMS (cation) m / z, 57 3 [M + H] +, 595 [M + Na] +. HRFABMS, C33H6407Na Calculated 値: 595. 4550 〇 Found: 595. 454 1. (6) (E) —1-propenyl 2-O-[(R) —3-hydroxytetradecyl] -3—O-decyl—a-D-glucopyranoside (Project A a 6) The compound (5) (210 mg, 0. 367 mmol) was dissolved in tetrahydrofuran (THF, 4 mL), hydrogen-activated Ir [C8H12 (MePh2P) 2] PF6 (5 mg) was added, and the mixture was stirred at room temperature overnight and concentrated to obtain the title compound (21 mg, quantitative). It can be used in the next reaction. 400 MHz! H NMR (CDC13) δ 0. 88 (6H, t, J = 6. 6 Hz), 1. 26 (32H, bs), 1. 41-1. 73 (9H, m), 1. 87 (1H, br, OH), 2. 47 (1H, br, OH), 2. 74 (1H, bs, OH), 3. 32 (1H, m), 3. 54-3. 92 (10H, m), 5.17 (1H, d, J = 3. 7 Hz), 5. 20 (1H, m), 6. 19 (1H, J = 1. 5 ’2. 5 Hz). FABMS (cation) m / z, 57 3 [M + H] +, 595 [M + Na] + · (7) (E) — 1 monopropanyl 6 — 〇3rd dimethylate One 3 —O —decyl — 2 — 0 — [(R) — 3 —Cetyltetradecyl] —α —D — [I Gluconoside (Section A a7) , 0. 349mmol) was dissolved in Dichloromethane Institute 200413400 (4 m L). 384 mmol) and DMAP (47 mg, 3 8 4 mmol), stirred at room temperature overnight, and then purified by silica gel chromatography. The mixed solution was dissolved in cyclohexane-ethyl acetate (4: 1) to obtain the title compound (217 mg, yield 90%) as an oil. IR vmax (film) 3456 (width), 2926, 2855, 1465 cm-1 · 400 MHz] H NMR (CDC13) δ 0. 08 (6H, s), 0. 88 (6H, t, J = 6. 6 Hz), 0. 90 (9H, s), 1. 26 (32H, bs), 1. 40- 1. 75 (9H, m, including 3H, d, J = 7. 3 Hz at 1. 55 ppm), 2. 75 (1H, bs? OH), 2. 84 (1H, bs, OH), 3. 30 (1H, m), 3. 53-3. 87 (10H, m), 5. 14 (1H, · d, J = 2. 9 Hz), 5. 20 (1H, m6. 20 (1H, d, J = 12. 5 Hz). FABMS (cation) m / z, 687 [M + H] +, 709 [M + Na] 'HRFABMS C39H78〇7SiNa Calculated 値: 709. 54 14. Found 値: 709. 5393. (8) (E) —1-propenyl 4-O-allyloxycarbonyl- 2-0 — [(R) —3- (allyloxycarbonyloxy) tetradecyl] —6--0— Tributyldimethylsilyl) 3-0-decyl-α-D-glucopyranoside (Project A a 8) _ will be the compound obtained in (7) (203mg, 0. 293 mmol) was dissolved in toluene (6 mL), and the ratio was adjusted to 0.1%. 5 0 g, 6 · 3 2 m m ο 1), add phosgene (200mg, 0. 674 mmol), and stirred vigorously for 10 minutes. Add strip propanol (0. 60g, 10. 331 mmol) and stirred for 1 hour under ice cooling. The reaction solution was diluted with ethyl acetate, washed with a sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration and concentration, purification was performed by silica gel column chromatography. Dissolve in cyclohexane-ethyl acetate (14: 1) to obtain the title compound and an unknown mixture (-85-200413400 3 2 5mg). It can be used in the next reaction. (9) (E) — 1-propenyl 4- 10-allyloxycarbonyl — 2 — 0 — [(R) — 3— (allyloxycarbonyloxy) tetradecyl] _3-O-decyl— α-D-glucopyranoside (Project A a9) The mixture (325) obtained in (8) was dissolved in dichloromethane (2. 5mL) and acetonitrile (5. (0mL), and added silica gel powder (1001 ^) and 48% hydrofluoric acid aqueous solution (100mg), stirred at room temperature for 30 minutes, and then diluted with dichloromethane. Wash with sodium bicarbonate solution and brine, and dry under magnesium sulfate. After filtration and concentration, it was purified by silica gel column chromatography. Dissolve in cyclohexane-ethyl acetate (2: 1) to obtain the title compound (126 mg, 2 engineering yield 58%). IR vmax (film) 3527 (width), 2926, 2855, 1 747, 1 678 (w) cm · 1. 400 MHz lH NMR (CDC13) δ 0. ******. 90 (6H, m), 1. 26 (32H, bs), 1. 50- 1. 68 (7H, m), 1 · 8 8 -1 · 9 2 (2 H, m), 2 · 3 4 (1H, bs, OH), 3.37 (1H, m), 3. 57-3. 78 (8H, m), 4. 60-4. 80 (6H, m), 5. 13-5. 40 (6H, m), 5. 90-5. 95 (2H, m), 6. 16 (1H, qd, J = i. 5, 12. 5 Hz). FABMS (HHi) m / z9 763 [M + Na] +. HRFABMS iNa calculation 値: 763. 4973. Found 値: 7 63. 4962. (10) (E)-1-propanyl 2-0— [(R) — 3- (dilute propoxyloxy) tetradecyl] -6-0— [2 —deoxy-1 4—0— Diallylphosphonic acid group 3-0-[(R) -3-methoxydecyl] -6-0-methyl-2 2-[(trichloroethoxycarbonyl) amino] -β-D-pyridine Glucosyl]-3-0-decyl-α-D-glucopyranoside (Project C a 1) -86-200413400 Trichloromethyliminofluorenyl 2-deoxy-4 -0- Diallylphosphonic acid group 3-0-[(R) -3-methoxydecyl] -6-0-methyl-α, β-D-glucopyranoside (180mg, 0. 2 13 mmol) and the compound obtained in (9) (158 mg, 0.1 187 mmol) was dissolved in dichloromethane (5 mL), and molecular sieves 4 A (400 mg) and AgOTf (100 mg, 0.1%) were added. 389mmol) and TMSOTf (10mg, 0. 045 mmol), and stirred at room temperature under nitrogen for 6 hours. The reaction solution was diluted with dichloromethane, washed with a sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated, and purified by silica gel chromatography. The title compound was obtained by dissolving cyclohexane-ethyl acetate (2: 1) (283 mg, yield 93%). IR vmax (film) 3400-3080, 2926, 2855, 1744 cm] · 400 MHz lU NMR (CDC13) δ 0. 88 (9H, t, J = 6. 6 Hz), 1. 25 (44H, bs), 1. 40- 1. 77 (9H, m, including 3H, dd, J = 1. 5, 6 ,. 6 Hz at 1. 55 ppm), 1. 87- 1. 89 (2H, m), 3. 24 (1H, m), 3.28 (3H, s), 3. 32 (1H, dd, J 2 3. 7, 9. 5 Hz), 3. 39 (3H, s), 3. 4 0-3 · 8 0 (1 4 H, m), 4. 05 (1H, d, J = 1 1. 7 Hz), 4. 26 (1H, m), 4. 50-4. 88 (1 2H, m), 5. 12 (1H, d, J = 2. 9 H z), 5. 1 6 (1 H, d d, J = 6. 6, 12. 5 Hz), 5. 70 (1H, brosd), 5. 21-5. 46 (8H, m), 5. 70 (1H, m), 5. 89-5. 98 (4H, m), 6. 16 (1H, qd, J = 1. 5, 12. 5 Hz), 6. 68 (1H, wide, NH). FABMS (cation) m / z, 1442 [M + Na, 35C1] +, 1444. HRFABMS C68H 1 1 7 3 5 C13N021P Calculation ... 1442. 68 1 9. Found 値: 1442. 6820. (11) (E) — 1—propanyl 4—O—granyloxy group — 2 — 〇 — -87 — 200413400 “(R) — 3— (nanopropoxyloxy) tetradecyl” — 3-0—decyl ~ 6— 〇— [2 —deoxy—4—0—one-burning propionate—3—0 — [(R) —3—methoxydecyl] —6—0—form 2-((Z) —11- (octadecylsulfanyl) amino] -β-D-pyranoglucoside] -pyranoglucoside (Ca2 project) will be (10 ) The compound obtained (95 2mg, O. 6 6 9 mmol) was dissolved in dry THF (21 mL), acetic acid (14 mL) and zinc metal (800 mg) were added, and the mixture was stirred vigorously for 3 hours. The reaction solution was concentrated by filtration, diluted with ethyl acetate, washed with sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. The solution was concentrated by filtration, and the obtained primary amine was dissolved in THF (4 mL). Water (0.1 mg) containing sodium bicarbonate (100 mg) was added. 9mL) and 1 1-octadecenoic acid chloride (227mg, 0. 803 mmol) of T H F (4 mL), and stirred vigorously at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate, washed with a sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. The solution was concentrated by filtration and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (3: 2) to obtain the title compound (439mg, yield 43%) and unknown structure (260mg) ° IR vmax (membrane) 3 308 (w), 3086 (w), 2926, 285 6, 1 748, 1 677, 1 6 6 0 cm'1. 400 MHz! H NMR (CDC13) δ 0. ******. 90 (12H, m), 1. 25 (62H, bs), 1. 40- 1. 80 (1 3H, m, including 3 H, d d, J = 1. 5, 6 · 6 H z a t 1. 54 ppm), 1. 82- 1. 89 (2H, m), 1. 98-2. 02 (4H, m), 2. 22-2. 26 (2H, m), 3. 22-3 · 79 (20H, m, including 3 H, s, at 3 · 2 8 p p m, an d 3 H, s, at 3. 37 ppm), 3. 84 (1H, m), 4. 04 (1H, m), 4. 23 (1H, m), 4. 53- -88-200413400 4. 87 (12H? M), 5. 03-5. 3 8 (1 2H, m)? 5. 88-5. 97 (4H, m), 6. 05 (1H, m), 6. 13 (1H, qd, J = 1. 5, 12. 5 Hz). FABMS (cation) m / z, 1 532 [M + Na] + · HRFABMS CnHMsNOnPNa Calculated 値: 1 5 3 3. 0230. Found 値: 1533. 0239. (12) 4— 0—_ propoxyfluorenyl — 2 — 0 — [(R) — 3 — (allyloxycarbonyloxy) tetradecyl] — 3-0 — decyl — 6 — 0 — [2 —Deoxy-4—10—diallylphosphonic acid—3—0 — [(R) —3—methoxydecyl] —6—O—methyl—2 — [(Z) — 11- (ten Octacarbenyl) amino]] β-D-glucopyranosyl] -α-D-glucopyranoside (Project C a 3) The compound (410 mg, 0.1 288 mmol) in dichloromethane (7. 7mL) —acetonitrile (16. 8mL), add 48% hydrofluoric acid (5. 25 mL) and stirred at room temperature overnight. The reaction was diluted with ethyl acetate to weigh. . Wash with sodium carbonate solution and saturated brine, and dry under magnesium sulfate. It was concentrated by filtration and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (1: 1 and 1: 3) to obtain the title compound (300 mg, yield 75%) as a gel. IR vmax (film) 3297 (w), 3086 (w), 2927, 285 6, 1 748, 1 65 2, 1 550, 1464 cm'1. 400 MHz lH NMR (CDC13) δ 0. ******. 89 (1 2H, m), 1. 25 (62H, bs), 1. 40- 1. 90 (1 3H, m, including OH), 1. 92-2. 02 (4H, m), 2. 17-2. 23 (2H, m), 3 · 1 0-3. 7 4 (2 OH, m, containing 3 H, s, at 3. 1 7 pp m, a n d 3H, s, at 3. 37 ppm), 3. 88-4. 70 (14H, m), 4. 81 (1H, m), 200413400 5. 18-5. 42 (11H? M), 5. 89-6. 00 (4H, m), 6. 09 (1H, d, J = 7. 3 Hz, NH). FABMS (cation) m / z, 1492 [M + Nal] +. HRFABMS, C800H144N02PNA calculation: 149: 9 9 17. Found 値: 149. 9875. (13) diallylphosphonic acid group 4-0—allyloxycarbonyl group 2-0 — “(R) — 3— (allyloxycarbonyloxy) tetradecyl” 3—0—decyl-6 10- [2—Deoxy-4—0—Diallylphosphonic acid group—3—0 — [(R) —3—Methoxydecyl] —6—0—methyl—2— [(Z) — 11- (octadecenyl) amino]] β-D-glucopyranosyl] -α-D-glucopyranoside (alpha form) and diallylphosphonic acid group Propoxycarbonyl- 2 — 0 — “(R) — 3— (allyloxycarbonyloxy) tetradecyl” —3-0—decyl-6 — 0— [2 -deoxy—4—0—two Allylphosphonic acid—3-0 — [(R) —3-methoxydecyl] —6—0—methyl—2 — [(Z) — 11— (octadecenyl) amino] -Β-D-glucopyranosyl]-β-D-glucopyranoside (β-body) (Project Ca4) (a) the compound of (12) (300mg, 0. 199mmol) was dissolved in dichloromethane (12mL), Na2S04 (630mg), 1H-tetrazole (460mg, 6. 57 mmol) and diisopropylamino diphosphate (510 mg, 2. 08 mmol), and stirred at room temperature under nitrogen for 30 minutes, and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (1: 1) to obtain oily diallylphosphonic acid group 4-10-allyloxycarbonyl group 2-0-"(R) — 3- (allyloxycarbonyl (Oxy) tetradecyl "— 3 — 0 -decyl-6 — 0 — [2-deoxy — 4 — 0 —diphosphinophosphonic acid — 3 — 0 — [(R) — 3 —methoxydecane []] -90-200413400 —6 — 0 —methyl-1 — [(Z)-11 (octadecenyl) amino]-β-D-glucopyranosyl]-D-pyran Glucoside (268 mg, 81% yield). It can be used in the next reaction. (b) the compound obtained by (a) 17 mmol) was dissolved in THF (25 mL), 30% H2O2 (500 mg) was added, and the mixture was stirred under ice cooling for 30 minutes, and then diluted with ethyl acetate. It was washed with 0% thiosulfuric acid water and brine, and dried over magnesium sulfate. It was concentrated by filtration and purified by silica gel chromatography. After dissolution with cyclohexane-ethyl acetate (1: 1 and then 1: 1), the title compound β-body (122 mg, yield 47%) and α-body (99 mg, yield 38%) were obtained as an oil. β-body: IR vmax (membrane) 3310 (w), 3086 (w), 2926, 2856, 1748, 1 677, 1551, 1 4 6 3 cm " 1. 400 MHz lH NMR (CDC13) δ 0. 80- 1. 90 (1 2H, m), 1. 26 (62H, bs), 1. 40-1. 75 (10H, m), 1. 80-1. 90 (2H, m), 1. 99-2. 05 (4H, m), 2. 20-2. 22 (2H, m), 3. 20 (1H, m), 3. 27 (3H? S), 3. 33 (1H, m), 3. 38 (3H, m), 3. 40-3. 80 (14H, m), 3. 99 (1H, m), Call 4. 25 (1H, m), 4. 49 (1H, t, J = 9. 5 Hz), 4. 55-4. 61 (11H, m), 4. 70 (1H, d, J = 8. 8 Hz), 4. 77 (1H, m), 4. 93 (1H, m), 5. 23-5. 43 (14H, m), 5. 86-5. 98 (6H, m), 7. 49 (1H, d, J = 10. 3 Hz, NH). FABMS (cation) m / z, 1 652 [M + Na] + · HRFABMS, C86Hi53N023P2Na Calculated 値: 1 6 5 3. 0 2 0 7 〇 Found 値: 1653. 0219. -91-200413400 Alpha body · IR vma "film" 3 303 (w), 308 6 (w), 2926, 2856, 1 747, 1 654, 1 546, 1464 cm-1. 400 MHz lR NMR (CDC13) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 25 (62H, bs), 1. 39- 1. 74 (10H, m), 1. 83- 1. 88 (2H, m), 1. 99-2. 02 (4H, m), 2. 21-2. 25 (2H, m), 3. 23 (1H, m), 3. 27 (3H, s), 3. 33 (1H, m), 3. 38 (3H, m), 3. 48-3. 77 (1 2H, m), 3. 83 (1H, dd, J = 8. 8, 9. 5 Hz), 3. 96 (1H, m), 4,01 (1H, m), 4. 25 (1H, dd, J = 9. 5, 18. 3 Hz), 4. 54-4. 61 (1 2 H, m), 4. 6 2-4. 7 3 (2H, m), 4. 76-4. 80 (1H, m), 5. 22-5. 41 (14H, m), 5. 71 (1H, dd, J = 2. 9, 6. 6 Hz), 5. 88-6. 01 (6H, m), 6. 51 (1H, d, J = 8. 1 Hz, NH). FABMS (cation) m / z, 1 652 [M + Na] + · HRFABMS, C86H153N023P2Na Calculated 値: 1 6 5 3. 0 2 0 7. Real S! L 値: 1653. 0184. (14) Phosphonic acid group 6-0— [2-deoxy-4—O—phosphonic acid group—3—〇 — [(R) —3—methoxydecyl] —6—O—methyl—2— [(Z) -11 (octadecenyl) amino] -β-D-glucopyranosyl] -3-3-0-decyl-2-0 — [(R) — 3_ Tetradecyl] a-D-0 glucopyranoside (Project C5) The α-form (90mg, 0. 055mmol) dissolved in anhydrous THF (6mL), PPh3 (15mg, 0. 057mmol), Et3N (60mg, 0. 593 mmol), HCOOH (51 mg, 1. 108mmol) and Pd (PPh3) 4 (15 mg, 0. 01 3 mmol), and stirred at 55 ° C for 20 hours under nitrogen. Reaction -92-200413400 After the end, it was filtered and concentrated, and purified with a column of DEA A-cellulose 8 g. Dissolution: 0 to CHCl3-Me0H-H20 (2: 3: 1). 05mol / L AcO_NH4 solution can get the part containing the target. Collect the mixture of the part and CHCl3-Me0H-H20 (1: 1: 1), and force in CHC13 and 0. 15mol / L hydrochloric acid water was stirred in a separatory funnel, and the lower CHC13 layer was collected and concentrated to obtain the title compound (53 mg, yield 74%) as a wax. IR vmax (KBr) 329 1 (w), 3076 (w), 2925, 2853, 1 628, 1 554, 14 6 6 cm " 1. 400 MHz lH NMR (C D C13-C D 3 O D, 5: 1) δ 0. ******. 90 (12H, m), 1. 27 (62H, bs)? 1. 40- 1. 75 (1 2H, m), 1. 99-2. 03 (4H, m), 2. 20-2. 26 (2H, m), 3. 23-4. 1 2 (26H, m, including 2 3H, s at 3. 30 and 3. 40 ppm), 4. 76 (1H, d, J = 8. 1 Hz), 5. 3 3-5. 39 (2H, m), 5. 7 1 (1H, dd, J = 3. 3, 7. 0 Hz). FABMS (anion) m / z, 1 300 [M-ΗΓ, 1 322 [M + Na-2H] 'HRFABMS, C66H128Noi9P2 Calculate 値 · 1 3 00 · 8 5 5 6 Found 値 1300. 8560. C66H129N019P2 Analysis and calculation: C, 60. 85; Η, 9. 98; N, 1. 08; P, 4. 76. Found 値: C, 60. 41; H, 10. 17; N, 1.09; P, 4. 54. [Example 2] Phosphonic acid group 6-0- [2-deoxy-4-0-phosphonic acid group 3-0-[(R) -3-methoxydecyl] -6-0-methyl-1 2 — [(Z) -11- (octadecenyl) amino] -β-D-glucopyranosyl]-3-0-decyl-2-0- [(R)-3- Hydroxytetradecyl] -β-D-glucopyranoside (Project C a 5) -93-200413400 The β-body (I12mg, 0. 069 mmol), and reacted according to the method of Example 1 (14) to obtain the title compound (72 mg, yield 80%) as a wax. IR vmax (KBr) 3 286 (w), 3073 (w), 2925, 2854, 1 628, 1 556, 14 6 6 cm'1. 400 MHz lU NMR (C D C13-C D 3 0 D, 5: 1) δ 0. ******. 90 (12H, m), 1.27 (62H, bs), 1. 40- 1. 80 (1 2H, m), 2. 00-2. 08 (4H, m), 2.24-2 · 28 (2H, m), 3. 1 3-4. 06 (26H, m, including 2 3H, s at 3. 30 and 3. 40 ppm), 4 · 9 2-4 · 9 7 (2 H, m), 5 · 3 4-5 · 3 8 (2 H, m) · FABMS (anion), m / z, 1 300 [MH] ·· C66H129N019P2 Analysis and calculation 値: c, 60. 85; H, 9. 98; N, 1. 08; P, 4 · 7 6. Measured 値: C, 6 0 · 3 6; H, 1 0. 1 7; N, 1 · 1 2; P, 4 · 6 8. [Example 3] Glucosanoic acid group 3-O-decyl-6-0- [2-Deoxy-4—O-phosphonic acid group 3—O — [(R) —3—methoxydecyl] — 6 — Ο monomethyl 2 — [(Z)-11 (octadecenyl) amino] — β — D —pyranosyl] — 2 — 0 — tetradecyl — α — D —Glucopyranoside (1) propyl 3 — 0 —decyl-4 ′ 6-0 — isopropylidene — 2 — 0 tetradecyl — a — D — glucopyranoside (Project A a4 ) The β-body obtained in Example 1 (3) (5. 15g, 12. 86m m 〇1) and 1- (methanesulfonyloxy) tetradecane (4. 51g, 15. 43mmol) was dissolved in DMF (25mL) solution, and sodium hydride (55% oil, 67〇11 ^, 15. 43111111〇1). According to the method of Example 1 (4), the title compound (7. 02g, yield 92 2%). -94-200413400 400 MHz! H NMR (CDC13) δ 0. 88 (6H, t, J = 6. 6 Hz), 1. 26 (36H, bs), 1. 40 (3H, s), 1. 47 (3H, s), 1. 50- 1. 60 (4H, m), 3. 10-4. 35 (12H, m), 4. 37 (1H, d, J = 8. 1 Hz), 5. 17-5. 34 (2H, m), 5. 91 (1H, m) · (2) Allyl 3-O -decyl-2-O-tetradecyl-β-D-glucopyranoside (Project A a5) The compound (1) obtained (7 · 0 2 g, 1 1 · 7 6 mm ο 1), reacted according to the method of Example 1 (5) to obtain the title compound (5. 〇2g, 77% yield) 400 MHz! H NMR (CDC13) δ 0. 88 (6Η? T, J = 6. 6 Hz), 1. 26 (36H, bs), 1. 52- 1. 62 (4H, m), 2. 07 (1H, t, J = 6. 6 Hz, OH), 2. 46 (1H? D, J 2 2. 2 Hz, OH), 3. 1 0-4 · 2 2 (1 2 H, m), 4 · 3 8 (1 H, d, J = 8. 1 Hz), 5. 21-5. 35 (2H, m), 5. 92 (1H, m). (3) (E) — 1-propenyl 3 — O —decyl — 2 — O —tetradecyl — β-D-glucopyranoside (Project A a6) The compound obtained in (2) (2. 5 1 g, 4 · 5 1 m m ο 1), and reacted according to the method of Example 1 (6) to obtain the title compound (2. 05 g, yield 82%). 400 MHz NMR (CDC13) δ 0. 88 (6Η, t, J = 6. 6-7. 3 Hz), 1. 26 (36H, bs), 1. 53- 1. 60 (7H, m, including 3H, dd, J = 1. 5, 7. 3 Hz, at 1. 56 ppm), 2. 06 (1H, t, J = 6. 6 Hz, OH), 2. 44 (1H, d, J = 1. 5 Hz, OH), 3. 14-3. 92 (10H, m), 4. 52 (1H, d, J = 7. 3 Hz), 5. 12 (1H, m), 6. 21 (1 H, q d, J = 1.5 · 12. 5 Hz). (4) (E) —1-propenyl 3-O-decyl-2—O-tetradecyl-1 β-D-glucopyranoside (Project A a7) -95-200413400 The compound obtained in (3) (2. 45 g, 0.4 10m mol), according to the method of Example 1 (7), the title compound (2. 80g, yield 89%). 400 MHz NMR (CDC13) δ 0. 08 (6H, s), 0. ******. 90 (1 5H, f m, including 9H, s, at 0 · 89 ppm), 1. 26 (36H, bs), 1. 53- 1. 60 (7H, m), 3. 02 (1H, d, J = 2. 2 Hz, OH), 3. 13-3. 24 (2H, m), 3. 33 (1H, m), 3. 49-3. 89 (7H, m), 4. 47 (1H, d, J = 7. 3 Hz), 5. 11 (1H, m), 6. 20 (1H, dd, J = 1. 7, 12. 1 Hz). (5) (E) — 1 —propenyl 4 10-allyloxycarbonyl 6 — ◦ (tertiary butanesilyl) — 3 — 0 — decyl — 2 — 0 — tetradecyl — β One D-glucopyranoside (Project A a8) will be (4) the obtained compound 80g, 4.17mmol), reacted according to the method of Example 1 (8) to obtain the title compound (2. 99 g, yield 95%). 400 MHz] H NMR (CDC13) δ 0. 03 (6H, s), 0. ******. 89 (1 5H, m, including 9H, s, at 0. 87 ppm), 1. 25 (36H, bs), 1.5 Bu 1. 56 (7H, m), 3. 22 (1H, dd, J = 7. 8, 9. 9 Hz), 3. 35 (1 H, d d, J = 8. 8, 9 · 9 Hz), 3. 43 (1H, m), 3 · 5 2-3 · 8 1 (6 H, m), 4 · 4 5 (1 H, d, J = 7 · 8 Hz), 4. 60-4. 72 (3H, m), 5. 11 (1H, m), 5. 27 (1H, d, J = 10. 7 Hz), 5. 36 (1H, d, J = 18. 5 Hz), 5. 93 (1H, m), 6. 21 (1H, m). (6) (E) — 1-propenyl 4--0-allyloxycarbonyl — 3 — 0 — decyl — 2 — 0-tetradecyl — β-D-pyranoglucoside (A A 9 project ) The compound obtained in (5) (2.98 g, 3. 95 mmol), reacted according to the method of Example 1 (9) to obtain the title compound (2.16 g, yield 85%). -96-200413400 IR Vmax (film) 3453 (width), 2925, 2854, 1 757, 1681 cm · 1 · 400 MHz NMR (CDC13) δ 0. 86 (6H, t, J = 6. 6 Hz), 1.26 (36H, bs), 1. 50- 1. 60 (7H, m), 2. 20 (1H, dd, J = 5. 8, 8. 0 Hz), 3. 24 (1H, m), 3. 40 (1H, dd, J = 8. 8, 9. 5 Hz), 3. 45 (1H, m), 3. 54-3. 68 (3H, m), 3. 72-3. 82 (3H, m), 4. 51 (1H, d, J = 8. 1 Hz), 4. 64-4. 72 (3H, m), 5. 12 (1H, m), 5. 29 (1H, d, J = 10. 3 Hz), 5. 37 (1H, d, 18. 3 Hz), 5. 93 (1H, m), 6. 21 (1H, qd, J = 1. 5, 12. 5 Hz). FABMS (cation) m / z, 663 [M + Na] + · HRFABMS C37H6 8 0 8 Na Calculated 値: 663. 48 1 2. Found 値: 663. 4802. (7) (E)-1 monopropanyl 6 — 0— [2 —deoxy — 4 — 10 — diallylphosphonic acid — 3 — 0 ([R) — 3 —methoxydecyl] 6-0-methyl-2-[(trichloroethoxycarbonyl) amino] -β-D-glucopyranosyl] -3-0-decyl-2-0-tetradecyl-β-D —Pyranoside (Project C a 1) The compound (3 4 7 mg, 0.5 4 1 mm ο 1) obtained in (6) was reacted according to the method of Example 1 (10) to obtain the title compound ( 577mg, yield 89%) IR vmax (film) 3 3 60-3 1 90 (width), 2926, 285 6, 1754, 1 7 3 6, 1680 (w) cm " 1. 400 MHz lU NMR (CDC13) δ 0. 88 (9H, t, J = 6. 6 Hz), 1. 25 (48H, bs), 1. 43- 1. 76 (9H, m, including 3H, dd, J = 1. 5, 7. 3 Hz, at 1. 62 ppm), 3. 21 (1H, m), 3.27 (3H, s), 3.32 (1H, m), 3. 38 -97-200413400 (3H, s) 5 3. 40-3. 64 (9H, m), 3. 70-3. 79 (6H, m)? 3. 90 (1H? M), 4. 32 (1H, m), 4. 48 (1H, d, J = 7. 3 Hz), 4. 55-4. 66 (9H, m), 4. 84 (1H, m), 5. 11-5. 40 (6H, m), 5. 87-5. 98 (3H, m), 6.32 (1H, m), 6. 62 (1H, bs, NH). FABMS (cation) m / z, 1 342 [M + Na, 35C1] +, 1 344 · HRFABMS calculation 値: C64H113Cl3N018PNa calculation 値: 1 342. 6666. Measured 値: 1 3 4 2 · 6 6 8 7. (8) (E) —1 propranyl group — 4 — 0 — propoxycarbonyl — 2 — 0 — “(R) — 3 — (allyloxycarbonyloxy) tetradecyl — 3 — Ο-dec — 6 — 0 — [2 —deoxy — 4 — 0 —diallylphosphonic acid — 3 — 0 — [(R) — 3 —methoxydecyl] — 6 — 0 —methyl — 2 — [ (Z) -11- (octadecenyl) amino] -β-D-glucopyranosyl] -β-D-glucopyranoside (Project C2) The compound obtained in (7) ( 4 0 5 mg, 0 · 3 0 6 mm ο 1), reacted according to the method of Example 1 (11) to obtain the title compound (302 mg, yield 70%) ° IR vmax (film) 3292 (w), 2926, 2855, 1 755, 1 678, 1 652, 1 5 52, 1465 cnT1 · 400 MHz lU NMR (CDC13) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 20-1 · 74 (79H, m, including 3H, d, J = 7. 4 Hz, at 1. 56 ppm), 2. 0 Bu 2. 26 (6H, m), 3. 16-3. 32 (7H, m, including 3H, s, at 3.27 ppm), 3.37 (3H, s), 3. 50-3. 80 (1 2H, m), 3. 92 (1H, m), 4.04 (1H, t, J = 9. 5 Hz), 4. 12 (1H, m), 4.26 (1H, m), 4.44 (1H, d, J = 8. 1 Hz), 4. 53-4. 61 (4H, m), 4. 62-4. 66 (2H, m), 4. 89 (1H, d, J = 8. 1 -98-200413400

Hz), 5.10 (1H, m), 5.22-5.40 (8H, m), 5.89-5.98 (3H, m), 6.24 (1H, d, J=12.4 Hz). FABMS (陽離子）m/z，1432 [M + Na] + . HRFABMS C^HmNOwPNa 計算値：1433.0063。實測値： 1433.0048. (9) 4 一 O —烯丙氧羰基一 3 — O—癸基一 6 — Ο—〔2—去氧一 4一〇一二烯丙膦酸基一 3— 〇一〔（R) — 3—甲氧癸基〕—6 一 Ο 一甲基一 2 -〔（Ζ) — 11 —(十八碳細酸基）月女基〕一 β— D —吡喃葡糖基〕一 2— 0 —十四基一 β— D—吡喃葡糖（第C a 3工程）將（8 )所得化合物（600mg，0.425mmol )，依實施例1 (12)之方法反應，可得標題化合物（47 1 mg，產率81%) 〇 IR vmax(膜）3299 (w)，3085 (w)，2925，2854，1754，1 653， 1650，1465 cm'1. 400 MHz ]H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.25 (66H, bs), 1.40-1.80 ( 10H, m), 1.83-2.02 (4H, m), 2.17-2·22 (2H，m)，2.33 (1H，m)，3.10-3.36 (6H，m，含 3H，s，at 3.27 ppm)，3·38 (3H，s)，3.45-3.80 ( 1 2H，m)，3.81-4.10 (4H, m), 4.24-4.64 (8H, m), 5.15-5.39 (8H, m), 5.87-5.98 (3H, m), 6.10 (1H, m). FABMS (陽離子）m/z，1 392 [M + Na] + . HRFABMS C76H14〇N017PNa 計算値：1 3 92 · 97 5 7。實測値： 1392.9757. 200413400 (10)二烯丙膦酸基4一 0—烯丙氧羰基一 3 - 0—癸基一 6 — Ο—〔2—去氧—4一0— 二烯丙膦酸基一 3 — 0—〔（R) 一 3 一甲氧癸基〕—6 — 0 —甲基一 2 —〔（Ζ) — 11 — （十八碳烯醯基）胺基〕一 β— D-吡喃葡糖基〕一 2 - 0-十四基一 a— D—吡喃葡糖苷（α體）及二烯丙膦酸基 4 一 0-烯丙氧羰基—3— 0 —癸基—6— 0-〔2 —去氧—4— 0 —二細丙鱗酸基一3 — 0 —〔（R) — 3 一甲氧癸基〕一 6 — 0 —甲基一 2—〔（Ζ) - 11一（十八碳烯醯基）胺基〕一 β - D- 吡喃葡糖基〕一 2— 0 —十四基—β— D-吡喃葡糖苷（β體 _ )(第C a 4工程） (a )將（9)所得化合物（214mg，0.156mmol)，依實施例1 ( 13 ) ( a )之方法反應，可得二烯丙膦酸基 4 一〇—烯丙氧羰基—3— Ο —癸基一6— Ο—〔2-去氧一 4 一 0 — 二烯丙膦酸基—3 — 0—〔（R) — 3-甲氧癸基〕—6— 0 —Hz), 5.10 (1H, m), 5.22-5.40 (8H, m), 5.89-5.98 (3H, m), 6.24 (1H, d, J = 12.4 Hz). FABMS (cation) m / z, 1432 [ M + Na] +. HRFABMS C ^ HmNOwPNa Calculated 値: 1433.0063. Measured fluorene: 1433.0048. (9) 4 -O-allyloxycarbonyl- 3 -O-decyl-6- 0- [2-deoxy-4-10-diallylphosphonic acid- 3-0- [ (R) — 3-methoxydecyl] -6 10-methyl- 2-[(Z) — 11 — (octadecyl fine acid group) pentyl]-β-D-glucopyranosyl ] 2-0-tetradecyl-1 β-D-glucopyranose (Project C a 3) The compound (600 mg, 0.425 mmol) obtained in (8) can be reacted according to the method of Example 1 (12). The title compound was obtained (47 1 mg, yield 81%). IR vmax (film) 3299 (w), 3085 (w), 2925, 2854, 1754, 1 653, 1650, 1465 cm'1. 400 MHz] H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.25 (66H, bs), 1.40-1.80 (10H, m), 1.83-2.02 (4H, m), 2.17-2 · 22 (2H, m ), 2.33 (1H, m), 3.10-3.36 (6H, m, including 3H, s, at 3.27 ppm), 3.38 (3H, s), 3.45-3.80 (1 2H, m), 3.81-4.10 ( 4H, m), 4.24-4.64 (8H, m), 5.15-5.39 (8H, m), 5.87-5.98 (3H, m), 6.10 (1H, m). FABMS (cation) m / z, 1 392 [ M + Na] +. HRFABMS C76H14〇N017PNa Calculate 値: 1 3 92 · 97 5 7. Found 値: 1392.9757. 200413400 (10) diallylphosphonic acid group 4-0-allyloxycarbonyl group 3-0-decyl-6-6-0- [2-deoxy-4-0-0 diallylphosphonic acid -3—0 — [(R) —3—methoxydecyl] —6—0—methyl—2 — [(Z) —11— (octadecenyl) amino] —β—D -Glucopyranosyl]-2-0-tetradecyl-a-D-glucopyranoside (alpha form) and diallylphosphonic acid group 4-0-allyloxycarbonyl-3-0-decyl —6— 0- [2 —Deoxy—4—0—Di-Fine Propionate—3—0 — [(R) —3—Methoxydecyl] —6—0—Methyl-2— [( (Z)-11- (octadecenyl) amino] -β-D-glucopyranosyl] -2-0-tetradecyl-β-D-glucopyranoside (β-body_) ( Project C a 4) (a) The compound (214 mg, 0.156 mmol) obtained in (9) is reacted according to the method of Example 1 (13) (a) to obtain diallylphosphonic acid group 4 10-allyl. Oxycarbonyl—3—O—decyl—6—O— [2-deoxy-4—0—diallylphosphonic acid—3—0— [(R) — 3-methoxy Yl] -6-0--

甲基一 2—〔（Z) - 11一（十八碳烯醯基）胺基〕一β— D 一吡喃葡糖基〕一 2— 0 —十四基一 D —吡喃葡糖苷（ 214mg，產率89% )。此可用於下一反應。參 (b )將（a )所得化合物（210mg，0.136mmol)，依實施例1 ( 13 ) ( b )之方法反應，可得β體（78mg，產率3 7 % )及α體（1 1 6 mg，產率5 5 % )之油狀物。 β體： IR vmax(膜）3 3 08 (w)，3 08 5 (w)，2926，2854，1 757，1 668， 1 550，1 464 cm·1. 400 MHz NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 -100 - 200413400 (66H，bs)，1.40- 1.75 ( 1 0H，m)，2.00-2.02 (4H，m)，2.10- 2.24 (2H，m)，3.18-3.80 (22H, m，含 2 個 3H，s, at 3.27 and 3.38 ppm), 4.00 (1H，m)，4.25 (1H，m)，4.56-4.63 ( 1 1H，m)， 4.70 (1H, d, J = 8.8 Hz), 4.95 (1H, d, J = 5.1, 8.1 Hz), 5.13 (1H，d，J = 8.1 Hz)，5.23-5.43 ( 1 2H, m)，5.86-5.99 (5H，m)， 7.50 (1H，d，J = 9.5 Hz，NH)· FABMS (陽離子）m/z，1 552 [M + Na] + . HRFABMS，C82H149N02〇P2 計算値：1 553.0046。實測値： 1553.0037. a體： IR vmax(膜）3305 (w)，3085 (w)，2925，2854，1 757，1 65 8， 1 548, 1465 cm'1. 400 MHz !H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (66H, bs), 1.40- 1.73 ( 10H, m), 2.00-2.05 (4H, m), 2.21- 2.25 (2H, rxi), 3.22-3.83 (22H，m，含 2 個 3H，s，at 3.28 and 3.38 ppm), 3.96-4.02 (2H, m), 4.25 (1H, m), 4.54-4.73 (11H, m), 5.23-5.40 ( 12H, m), 5.72 (1H, dd, J = 3.3, 6.2 Hz), 5.89-5.99 (5H, m), 6.50 (1H, d, J = 8.1 Hz, NH). FABMS (陽離子）m/z，1552 [M + Na] + . HRFABMS，C82H149N〇2〇P2 計算値：1 5 5 3 · 0046。實測値： 1553.0045. (11)膦酸基3 - O—癸基一 6— O-〔2—去氧一 4一 O — 膦酸基一3—0—〔（R) — 3—甲氧癸基〕一 6— Ο—甲基一 2—〔（ Ζ ) - 11一（十八碳嫌醯基）胺基〕一β - D-卩ϋ喃 -101 - 200413400 葡糖基〕一 2 - 0 —十四基一 α — D —吡喃葡糖苷（第C a5 工程）將（10)所得α體（75mg，0.04 9mmol)，依實施例1 ( 14)之方法反應，可得蠟狀標題化合物（54mg，產率86% )° IR vmax(KBr) 3290 (寬），3080 (w，broad)，2924，2853，1 630, 1 550，1 467 cm'1. 400 MHz NMR (CDCl3-CD3〇D, 4:1) δ 0.89 (12H, m), 1.27 (66H，bs)，1.40- 1.80 ( 10H，m)，2.01-2.03 (4H，m)， 2.24-2.26 (2H，m)，3.1 4-3.92 (23H, m,含 2 個 3H，s at 3.30 and 3.40 ppm), 3.92-4.1 1 (2H，m)，4.72 (1H，d，J = 8 · 8 Hz)， 5.34-5.39 (2H? m), 5.63 (1H, m). FABMS (陰離子）m/z，1 284 [Μ-ΗΓ. HRFABMS，C66H128N018P2 計算値：1 2 8 4.8 6 0 7。實測値： 1284.8607. C66H129N018P2 分析計算値：C，61.61; Η, 10.11; N，1.09; P， 4.81。實測値·· C, 59·72; Η, 9.44; Ν，1·10; P，4.12· 〔實施例4〕鱗酸基3 - Ο —癸基一 6 — Ο —〔2 —去氧一 4 — Ο —鱗酸基 — 3—0—〔 ( R) 一 3 —甲氧癸基〕一6— 0 —甲基一2—〔 (Ζ) — 11一（十八碳烯醯基）胺基〕一 β— D-吡喃葡糖基〕一 2— 〇 —十四基一 β— D—吡喃葡糖苷（第C a 5工程 ) 將實施例3 ( 10)所得β體（112mg，0.07 3mmol)，依實 -102 - 200413400 施例1 ( 1 4 )之方法反應，可得蠟狀標題化合物（6 1 mg, 產率6 5 % )。 IR vmax(KBr) 3 28 8 (寬），3072 (w，寬），2925，2854，1631， 1550, 1466 cm"1. 400 MHz ]H NMR ( C D C13 - C D 3 O D , 4:1) δ 0.88 (12H, t, J = 6.6 Hz), 1.27 (66H, bs), 1.40- 1.76 ( 10H, m), 2.00-2.04 (4H，m)，2.24-2.28 (2H，m)，3.1 1 -3.89 (23H，m，含 2 個 3H, s at 3.3 1 and 3.40 ppm), 4.00-4.07 (2H, m), 4.93-4.98 (2H, m), 5.3 3-5.36 (2H, m). · FABMS (陰離子）m/z，1 284 [Μ-ΗΓ，1 306 [M + Na-2Hr. HRFABMS，C66H128N〇i8P2 計算値：1 284.8607。實測値： 1284.8605. C66H129N018P2 分析計算値·· C，61.61; H，10.11; N，1.09; P， 4.81。實測値：C，61.22; H，10.38; N, 1.28; P, 4.74. 〔實施例5〕 2—（膦酸氧基）乙基 6— Ο—〔2—去氧—4— 0 —膦酸基一3— 0—〔（R) — 3 —甲氧癸基〕一6— 0 —甲基一2 — _ 〔（Z) - 11一（十八碳烯醯基）胺基〕一β - D-吡喃葡糖基〕—3— 0 —十二基—2— Ο - [(R) — 3 -羥基十四基] 一 α - D -吡喃葡糖苷 (1) 1’ 2: 5’ 6 — 一一 0 —亞異丙基—3 - 0 —十二基一 α - D—呋喃葡萄糖（第A a 1工程）將1，2: 5，6 —二—0 —亞異丙基—a— D —肤喃葡萄糖 (13.0g，5 0mmol )及 1—(甲磺醯氧基）十二烷（13.2g， -103 - 200413400 50mmol )溶在DMF ( 50mL )，於冰冷卻下加入氫化鈉（ 5 5 %油中，2.28 m g，60 mmol )。於0 °C下攪拌1 5分，再於室温攪拌過夜，於冰冷卻下加入甲醇以分解氫化鈉，以乙酸乙酯稀釋。以水及飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮後，進行矽膠層析純化。溶離以環己烷-乙酸乙酯 (9 : 1，再以4 : 1)，可得油狀標題化合物（I5.5g，產率 7 5%) 〇 400 MHz lU NMR (CDC13) δ 0.88 (3H, t, J = 6.6 Hz), 1.26 (18H, bs), 1.32 (3H, s), 1.35 (3H, s), 1.43 (3H, s), 1.50 (3H, s), 1.52- 1.57 (2H, m), 3.51 (1H, m), 3.59 (1H, m), 3.85 (1H, d, J = 2.9 Hz), 3.98 (1H, m), 4.06-4.14 (3H, m), 4.31 (1H, m), 4.52 (1H, d, J = 3.7 Hz), 5.88 (1H, d, J-3.7 Hz). (2)烯丙基3 - O—十二基—α — D —吡喃葡糖苷（第A a 2工程）將（1 )所得化合物（900mg, 2.160mmol)加入含2%鹽酸之烯丙醇（2 m 1 )，將反應液回流15分。將反應液濃縮，進行矽膠層析純化。溶離以環己烷-乙酸乙酯（1 : 1，再以1 : 3 )，可得油狀標題α體（674mg，產率80% )及β atm 體。 α體： 400 MHz lU NMR (CDC13) δ 0.88 (3H, t, J = 7.0 Hz), 1.26 (18H，bs)，1·59-1·64 (2H，m)，2.19 (1H，d，J = 9.5 Hz，OH)， 2.24 (1H, t, J = 6.3 Hz, OH), 2.79 (1H, d, J = 2.9 Hz, OH), -104 - 200413400 3.45 (1H, d, J = 8.8 Hz), 3.50-3.61 (2H, m), 3.64-3.71 (2H, m), 3.80-3.86 (2H? m), 3.93 (1H, m), 4.04 (1H, m), 4.23 (1H，m)，4.90 (1H，d, J = 3.7 Hz，異構物），5.22-5.34 (2H， m), 5.92 (1H, m). c 2 1 H 4 0 〇 6 分析計算値：c，6 4 · 9 2 ; H，1 0 · 3 8。實測値：C， 64.96; H， 10.17. β體： 400 MHz 4 NMR (CDC13 + D20) δ 0·88 (3H, t，J = 7.0 Hz)， 1.26 (18H, bs), 1.50-1.61 (2H, m), 3.46-4.53 ( 1 0H, m), 5.07 (1H，d，J = 5.1 Hz)，5.21-5.42 (2H, m)，5·93 (1H，m)· (3) 烯丙基3— O —十二基一 4，6 - O-亞異丙基一 a — D —吡喃葡糖苷（第A a 3工程）將（2)所得 α 體（4.70g，12.1mmol)溶於 D M F ( lOmL)，加入 2,2-二甲氧丙烷（l〇mL)及 p-TsOH ( 200mg )，於室温下攪拌1 6小時。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮，進行砂膠層析純化。溶離以環己院一乙酸乙酯（4 : 1 —2 : 1 )，可得油狀標題化合物（4.2 〇 g，產率8 1 % )。 400 MHz ^ NMR (CDC13) δ 〇.δ8 (3H, t, J = 6.6 Hz), 1.26 (18H，bs)，1·41 (3H，s)，1·49 (3jj，s)，1.53- 1.60 (2H，m)， 2.31 (1H，d，J = 7.3 Hz，OH)，3.46-3.85 (8H，m)，4.04 (1H， m)，4·21 (1H，m)，4.92 (1H，d，j = 3.7 Hz)，5·22-5·34 (2H, m), 5.93 (1H, m). (4) 烯丙基2 — O— [(R)〜3—(第三丁二甲矽烷氧基 -105 - 200413400 )十四基]—3— 0—十二基一 4，6— 0—亞異丙基一 a— D — 吡喃葡糖苷（第A a4工程）將（3 )所得化合物（3 5 8mg，O.8 3 5mmol)及（R) - 3-(第三丁二甲矽烷氧基）一 1一（甲磺醯氧基）十四烷（ 392mg，0.927mmol)溶在 DMF ( 3mL)，加入氫化鈉（55 % 油中，66mg，1.51 3mmol )。於室温攪拌過夜，於冰冷卻下加入甲醇以分解氫化鈉，以乙酸乙酯稀釋。以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（9 : 1 )，可得油狀標題化 _ 合物（510mg，產率81% )。 IR vmax(膜）2925，2856，1464 cm·1. 400 MHz ]H NMR (CDC13) δ 0.04 (6H, s), 0.86-0.89 ( 1 5H, m,含 9H, s, at 0.88 ppm), 1.26 (3 8H, broad s), 1.40 (3H, s), 1.48 (3H, s), 1.48- 1.55 (2H, m), 1.70- 1.77 (2H, m), 3.29 (1H, m), 3.47-3.78 (9H, m), 3.84 (1H, m), 4.04 (1H, m), 4.17 (1H, m), 4.91 (1H, d, J = 3.7 Hz), 5.20-5.34 (2H, m), 5.92 (1H, m). · FABMS m/z, 755 [M + H] + . HRFABMS C44H8607SiNa 計算値：777.6040。實測値： 777.5994. (5) 2 —羥乙基2— O— [(R) — 3—（第三丁二甲矽烷氧基）十四基]一 3 — 0 —十二基一 4，6— 0 —亞異丙基—α —D—吡喃葡糖苷（第Abl工程）將（4 )所得化合物（980mg, 0.230mmol )溶在THF — -106 - 200413400 H20 ( 7 ： 2, 30mL)，加入 NaI04 ( 1.8 0g)及 2· 5% 四氧化鎢之第三丁醇（0.5 0g)，於室温下攪拌2小時後，以乙酸乙酯稀釋。以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮可得醛殘渣。溶在乙醇（1 OmL )，加 Λ NaBH4 ( lOOmg)，攪拌20分。加入乙酸，以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷-乙酸乙酯（4 : 1)，可得油狀標題化合物（448 mg，產率41%) 之油狀物。 IR vmax(膜）3468 (寬），2926，2856，1465，1 380，1 3 70 cnT1· 400 MHz 2H NMR (CDC13) δ 0.04 (6H, s), 0.88 (9H, t, J = 6.6 Hz), 0.89 (6H, t, J = 6.3 Hz), 1.26 (36H, bs), 1.40 (3H，s), 1.4 卜 1.43 (2H, m)，l.48 (3H，s)，1.52- 1.56 (2H，m)， 1.71-1.75 (2H，m)，2.82 (1H，bs, OH), 3.30 (1H，m)，3.51-3.85 (14H，m)，4.89 (1 H，d, J = 3 · 7 H z). (6) 2 - [(二烯丙膦酸基）氧基]乙基 2— Ο — [(R) 一 3—（第三丁二甲矽烷氧基）十四基]—3 — Ο—十二基一 4 ，6— 0 —亞異丙基—α — D —吡喃葡糖苷（第Ab2工程）將（5 )所得化合物（428mg，0.564mmol )溶在 CH2C12 ( 7mL)溶液，加入1H —四哇（92mg)，二異丙胺基憐酸二嫌丙酯（277mg)及硫酸鈉（350mg)，於室温攪拌30分後，加入THF ( 7mL)及31%過氧化氫（2 00mg) ’於室温攪拌15分後’以乙酸乙酯稀釋，以1〇% Na2S2〇3水溶液，重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過 -107 - 200413400 濾濃縮，進行矽膠層析純化。溶離以環己烷-乙酸乙酯（2 ·· 1)，可得標題化合物（ 504mg，產率97%)。 IR vmax(膜）2927，285 6，1464 cm·1. 400 MHz 'H NMR (CDC13) δ 0.04 (6H, s), 0.88 (15H, bs), 1·26 (36H，bs), 1·39 (3H，s)，1.41-1.89 (12H, m)，4.22-4.27 (2H, m), 4.56-4.59 (4H, m), 4.88 (1H, d, J = 3.7 Hz), 5.21-5.41 (4H, m), 5.91-6.01 (2H, m). (7) 2 — [(二烯丙膦酸基）氧基]乙基 —3— 〇 —十二基—2— Ο — [(R) - 3 —羥基十四基]—a— D-吡喃葡糖苷鲁 (第A b 3工程）將（6)所得化合物（ 489mg，0.532mmol)溶在 MeOH( 6mL )，加入p-TsOH ( 3 5mg )，於室温攪拌2小時後濃縮，進行矽膠層析純化。溶離以乙酸乙酯，再溶離以10%Methyl-2-[(Z) -11- (octadecenyl) amino] -β-D-glucopyranosyl] -2-0-tetradecyl-D-glucopyranoside ( 214 mg, yield 89%). This can be used for the next reaction. According to (b), the compound (210 mg, 0.136 mmol) obtained in (a) was reacted according to the method of Example 1 (13) (b) to obtain β-body (78 mg, yield 37%) and α-body (1 1 6 mg, yield 55%). β-body: IR vmax (film) 3 3 08 (w), 3 08 5 (w), 2926, 2854, 1 757, 1 668, 1 550, 1 464 cm · 1. 400 MHz NMR (CDC13) δ 0.88 ( 12H, t, J = 6.6 Hz), 1.26 -100-200413400 (66H, bs), 1.40-1.75 (1 0H, m), 2.00-2.02 (4H, m), 2.10- 2.24 (2H, m), 3.18 -3.80 (22H, m, including 2 3H, s, at 3.27 and 3.38 ppm), 4.00 (1H, m), 4.25 (1H, m), 4.56-4.63 (1 1H, m), 4.70 (1H, d , J = 8.8 Hz), 4.95 (1H, d, J = 5.1, 8.1 Hz), 5.13 (1H, d, J = 8.1 Hz), 5.23-5.43 (1 2H, m), 5.86-5.99 (5H, m ), 7.50 (1H, d, J = 9.5 Hz, NH) · FABMS (cation) m / z, 1 552 [M + Na] +. HRFABMS, C82H149N02P2 Calculated 値: 1 553.0046. Measured 値: 1553.0037. Body A: IR vmax (film) 3305 (w), 3085 (w), 2925, 2854, 1 757, 1 65 8, 1 548, 1465 cm'1. 400 MHz! H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (66H, bs), 1.40- 1.73 (10H, m), 2.00-2.05 (4H, m), 2.21- 2.25 (2H, rxi), 3.22-3.83 (22H, m, including 2 3H, s, at 3.28 and 3.38 ppm), 3.96-4.02 (2H, m), 4.25 (1H, m), 4.54-4.73 (11H, m), 5.23-5.40 (12H, m), 5.72 (1H, dd, J = 3.3, 6.2 Hz), 5.89-5.99 (5H, m), 6.50 (1H, d, J = 8.1 Hz, NH). FABMS (cation) m / z, 1552 [ M + Na] +. HRFABMS, C82H149NO2P2 Calculated 値: 1 5 5 3 · 0046. Measured erbium: 1553.0045. (11) Phosphonic acid group 3-O-decyl-6-O- [2—deoxy-4—O—phosphonic acid group 3-0— [(R) — 3-methoxydecane Group]-6-0-methyl-1 2-[(Z)-11- (octadecylsulfanyl) amino] -β-D-galan-101-200413400 glucosyl] -2-0 —Tetradecyl —α — D —glucopyranoside (Project C a5) The α-form (75 mg, 0.04 9 mmol) obtained in (10) was reacted according to the method of Example 1 (14) to obtain the title compound as a wax. (54mg, yield 86%) ° IR vmax (KBr) 3290 (wide), 3080 (w, broad), 2924, 2853, 1 630, 1 550, 1 467 cm'1. 400 MHz NMR (CDCl3-CD3. D, 4: 1) δ 0.89 (12H, m), 1.27 (66H, bs), 1.40-1.80 (10H, m), 2.01-2.03 (4H, m), 2.24-2.26 (2H, m), 3.1 4 -3.92 (23H, m, including 2 3H, s at 3.30 and 3.40 ppm), 3.92-4.1 1 (2H, m), 4.72 (1H, d, J = 8 · 8 Hz), 5.34-5.39 (2H? m), 5.63 (1H, m). FABMS (anion) m / z, 1 284 [M-ΗΓ. HRFABMS, C66H128N018P2 Calculate 値: 1 2 8 4.8 6 0 7. Measured 値: 1284.8607. C66H129N018P2 Analytical calculation: ，: C, 61.61; Η, 10.11; N, 1.09; P, 4.81. Measured 値 ·· C, 59 · 72; Η, 9.44; Ν, 1 · 10; P, 4.12 · [Example 4] Lithonic acid group 3-Ο -decyl-6-Ο-[2 -deoxy-4 — Ο —Scaleno — 3 — 0 — [(R) — 3 —methoxydecyl] — 6 — 0 —methyl — 2 — [(Z) — 11 (octadecenyl) amino 〕 -Β-D-glucopyranosyl] -2-0-tetradecyl-β-D-glucopyranoside (Project C a 5) The β-body (112 mg, 0.07) obtained in Example 3 (10) 3 mmol), according to the method of Example-102-200413400 Example 1 (14), the title compound was obtained as a wax (61 mg, yield 65%). IR vmax (KBr) 3 28 8 (width), 3072 (w, width), 2925, 2854, 1631, 1550, 1466 cm " 1. 400 MHz] H NMR (CD C13-CD 3 OD, 4: 1) δ 0.88 (12H, t, J = 6.6 Hz), 1.27 (66H, bs), 1.40- 1.76 (10H, m), 2.00-2.04 (4H, m), 2.24-2.28 (2H, m), 3.1 1 -3.89 (23H, m, including 2 3H, s at 3.3 1 and 3.40 ppm), 4.00-4.07 (2H, m), 4.93-4.98 (2H, m), 5.3 3-5.36 (2H, m). · FABMS ( Anion) m / z, 1 284 [M-ΗΓ, 1 306 [M + Na-2Hr. HRFABMS, C66H128N0i8P2 Calculated 値: 1 284.8607. Measured 値: 1284.8605. C66H129N018P2 Analytical calculation 値 · C, 61.61; H, 10.11; N, 1.09; P, 4.81. Measured rhenium: C, 61.22; H, 10.38; N, 1.28; P, 4.74. [Example 5] 2- (phosphonooxy) ethyl 6-0- [2-deoxy-4-0-phosphonic acid A group of 3-0 — [(R) —3—methoxydecyl] —6—0—methyl—2— — [(Z)-11- (octadecenyl) amino]] β- D-glucopyranosyl] -3-0-dodecyl-2-O-[(R) — 3-hydroxytetradecyl] -α-D-glucopyranoside (1) 1 '2: 5 '6 — one to ten — isopropylidene — 3 — 0 — dodecyl — α — D — furanose (Project A a 1) will be 1,2: 5, 6 — two — 0 — isopropylidene —A— D —glucopyranose (13.0g, 50mmol) and 1- (methanesulfonyloxy) dodecane (13.2g, -103-200413400 50mmol) were dissolved in DMF (50mL) and added under ice cooling Sodium hydride (55% oil, 2.28 mg, 60 mmol). Stir at 0 ° C for 15 minutes, and stir overnight at room temperature. Add methanol to decompose sodium hydride under ice cooling, and dilute with ethyl acetate. It was washed with water and saturated brine, dried over magnesium sulfate, concentrated by filtration, and then purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (9: 1, then 4: 1) to obtain the title compound (I5.5g, yield 75%). 〇400 MHz 1U NMR (CDC13) δ 0.88 (3H , t, J = 6.6 Hz), 1.26 (18H, bs), 1.32 (3H, s), 1.35 (3H, s), 1.43 (3H, s), 1.50 (3H, s), 1.52- 1.57 (2H, m), 3.51 (1H, m), 3.59 (1H, m), 3.85 (1H, d, J = 2.9 Hz), 3.98 (1H, m), 4.06-4.14 (3H, m), 4.31 (1H, m ), 4.52 (1H, d, J = 3.7 Hz), 5.88 (1H, d, J-3.7 Hz). (2) Allyl 3-O-dodecyl-α-D-glucopyranoside (No. A a 2 project) The compound (900 mg, 2.160 mmol) obtained in (1) was added to allyl alcohol (2 m 1) containing 2% hydrochloric acid, and the reaction solution was refluxed for 15 minutes. The reaction solution was concentrated and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (1: 1, then 1: 3) to obtain the title alpha form (674 mg, yield 80%) and beta atm form as an oil. Alpha body: 400 MHz lU NMR (CDC13) δ 0.88 (3H, t, J = 7.0 Hz), 1.26 (18H, bs), 1.59-1 · 64 (2H, m), 2.19 (1H, d, J = 9.5 Hz, OH), 2.24 (1H, t, J = 6.3 Hz, OH), 2.79 (1H, d, J = 2.9 Hz, OH), -104-200413400 3.45 (1H, d, J = 8.8 Hz) , 3.50-3.61 (2H, m), 3.64-3.71 (2H, m), 3.80-3.86 (2H? M), 3.93 (1H, m), 4.04 (1H, m), 4.23 (1H, m), 4.90 (1H, d, J = 3.7 Hz, isomers), 5.22-5.34 (2H, m), 5.92 (1H, m). C 2 1 H 4 0 〇6 Analytical calculation 値: c, 6 4 · 9 2 ; H, 1 0 · 38. Measured 値: C, 64.96; H, 10.17. Β-body: 400 MHz 4 NMR (CDC13 + D20) δ 0 · 88 (3H, t, J = 7.0 Hz), 1.26 (18H, bs), 1.50-1.61 (2H , m), 3.46-4.53 (1 0H, m), 5.07 (1H, d, J = 5.1 Hz), 5.21-5.42 (2H, m), 5.93 (1H, m) · (3) allyl 3-O-dodecyl-4,6-O-isopropylidene-a-D-glucopyranoside (Project A a 3) The α-form (4.70 g, 12.1 mmol) obtained in (2) was dissolved DMF (10 mL), 2,2-dimethoxypropane (10 mL) and p-TsOH (200 mg) were added, and the mixture was stirred at room temperature for 16 hours. The reaction solution was diluted with ethyl acetate, washed with a sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated, and purified by silica gel chromatography. The ethyl acetate (4: 1-2: 1) was dissolved in cyclohexane to obtain the title compound (4.20 g, yield 81%) as an oil. 400 MHz ^ NMR (CDC13) δ 〇.δ8 (3H, t, J = 6.6 Hz), 1.26 (18H, bs), 1.41 (3H, s), 1.49 (3jj, s), 1.53- 1.60 (2H, m), 2.31 (1H, d, J = 7.3 Hz, OH), 3.46-3.85 (8H, m), 4.04 (1H, m), 4.21 (1H, m), 4.92 (1H, d , J = 3.7 Hz), 5.22-5 · 34 (2H, m), 5.93 (1H, m). (4) Allyl 2 — O— [(R) ~ 3— (Third butadiene Silyloxy-105-200413400) tetradecyl] -3-0-dodecyl-4,6--0-isopropylidene-a-D-glucopyranoside (Project A a4) will (3) The obtained compound (3 5 8 mg, 0.8 3 5 mmol) and (R) -3- (tertiary butanesilyloxy) -l- (methanesulfonyloxy) tetradecane (392 mg, 0.927 mmol) were dissolved. In DMF (3 mL), sodium hydride (55% oil, 66 mg, 1.51 3 mmol) was added. After stirring at room temperature overnight, methanol was added under ice-cooling to decompose sodium hydride, and diluted with ethyl acetate. Wash with water and saturated brine and dry under magnesium sulfate. The solution was concentrated by filtration and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (9: 1) to obtain the title compound (510 mg, yield 81%) as an oil. IR vmax (film) 2925, 2856, 1464 cm · 1. 400 MHz] H NMR (CDC13) δ 0.04 (6H, s), 0.86-0.89 (1 5H, m, including 9H, s, at 0.88 ppm), 1.26 (3 8H, broad s), 1.40 (3H, s), 1.48 (3H, s), 1.48- 1.55 (2H, m), 1.70- 1.77 (2H, m), 3.29 (1H, m), 3.47-3.78 (9H, m), 3.84 (1H, m), 4.04 (1H, m), 4.17 (1H, m), 4.91 (1H, d, J = 3.7 Hz), 5.20-5.34 (2H, m), 5.92 ( 1H, m). · FABMS m / z, 755 [M + H] +. HRFABMS C44H8607SiNa Calculated 値: 777.6040. Found 値: 777.5994. (5) 2-Hydroxyethyl 2-O-[(R) — 3 -— (Third-butadisilyloxy) tetradecyl] —3—0—Dodecyl—4,6 — 0 —isopropylidene—α —D-glucopyranoside (Abl project) The compound (980 mg, 0.230 mmol) obtained in (4) was dissolved in THF — -106-200413400 H20 (7: 2, 30 mL), NaI04 (1.80 g) and 2.5% tertiary butanol (0.50 g) of tungsten tetraoxide were added, and the mixture was stirred at room temperature for 2 hours, and then diluted with ethyl acetate. It was washed with sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. The aldehyde residue was obtained by filtration and concentration. Dissolve in ethanol (10 mL), add ΛNaBH4 (100 mg), and stir for 20 minutes. Add acetic acid, dilute with ethyl acetate, wash with sodium bicarbonate solution and saturated brine, and dry with magnesium sulfate. It was concentrated by filtration and purified by silica gel chromatography. The title compound (448 mg, yield 41%) was obtained as an oil by dissolution with cyclohexane-ethyl acetate (4: 1). IR vmax (film) 3468 (wide), 2926, 2856, 1465, 1 380, 1 3 70 cnT1 · 400 MHz 2H NMR (CDC13) δ 0.04 (6H, s), 0.88 (9H, t, J = 6.6 Hz) , 0.89 (6H, t, J = 6.3 Hz), 1.26 (36H, bs), 1.40 (3H, s), 1.4, 1.43 (2H, m), 1.48 (3H, s), 1.52- 1.56 (2H , M), 1.71-1.75 (2H, m), 2.82 (1H, bs, OH), 3.30 (1H, m), 3.51-3.85 (14H, m), 4.89 (1 H, d, J = 3 · 7 H z). (6) 2-[(Diallylphosphonicyl) oxy] ethyl 2—O — [(R) 3— (Third-butadisilyloxy) tetradecyl] -3 — 〇—Dodecyl-4,6-0—Isopropylidene—α—D—Gluconoside (Project Ab2) Dissolve the compound obtained in (5) (428mg, 0.564mmol) in a solution of CH2C12 (7mL) Add 1H-tetra wow (92mg), diisopropylaminophosphonate (277mg) and sodium sulfate (350mg), stir at room temperature for 30 minutes, then add THF (7mL) and 31% hydrogen peroxide (2 00mg) 'After stirring at room temperature for 15 minutes', it was diluted with ethyl acetate, washed with 10% aqueous Na2S203 solution, sodium bicarbonate solution and saturated saline, and dried over magnesium sulfate. Filter through -107-200413400 and concentrate for purification by silica gel chromatography. The title compound was obtained by dissolving cyclohexane-ethyl acetate (2 ·· 1) (504 mg, yield 97%). IR vmax (film) 2927, 285 6, 1464 cm · 1. 400 MHz 'H NMR (CDC13) δ 0.04 (6H, s), 0.88 (15H, bs), 1.26 (36H, bs), 1.39 (3H, s), 1.41-1.89 (12H, m), 4.22-4.27 (2H, m), 4.56-4.59 (4H, m), 4.88 (1H, d, J = 3.7 Hz), 5.21-5.41 (4H , m), 5.91-6.01 (2H, m). (7) 2 — [(Diallylphosphono) oxy] ethyl — 3 — 0 —dodecyl — 2 — 0 — [(R)- 3-Hydroxytetradecyl] -a-D-glucopyranoside (Project A b 3) The compound (489 mg, 0.532 mmol) obtained in (6) was dissolved in MeOH (6 mL), and p-TsOH (35 mg ), Stirred at room temperature for 2 hours, then concentrated, and purified by silica gel chromatography. Dissolve with ethyl acetate, then dissolve with 10%

MeOH乙酸乙酯溶液，可得蠟狀之標題化合物（34〇mg，產率 8 4 % )。 IR vmax(膜）3388，（寬），29 1 8, 2850, 1467 cnT1· 400 MHz ]H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 # (36H，bs)，1.4 卜 1.73 (6H，m)，2.56 (1H，m，OH)，2.68 (1H, d，J = 2.9 Hz，OH)，3.12 (1H，bs，OH)，3·29 (1H，m)，3 44_ 3.92 (12H，m)，4.22-4.28 (2H，m)，4.55-4.59 (4H，m)，5.00 (1H，d，J = 3.7 Hz)，5.25-5.28 (2H，m)，5·35-5·41 (2H, m， 5.90-6.00 (2H, m). (8) 2— [(二烯丙膦酸基）氧基]乙基6— O—〔2 —去氧一 4 一0—二烯丙膦酸基一3— Ο—〔（R) — 3—甲氧癸基〕一 -108 - 200413400 6 一〇 —甲基一 2 —〔（三氯乙氧羰基）胺基〕一 β— D—毗喃葡糖基〕一 3— Ο -十二基—2 — Ο— [(R) — 3—羥基十四基]—a— D-卩比喃葡糖甘（弟C b 1工程）將三氯甲基亞胺醯基2-去氧一 4一 Ο-二烯丙膦酸基—3 —Ο —〔（R) — 3 —甲氧癸基〕一 6 — Ο 一甲基一 α，β — D — 吡喃葡糖苷（360mg，0.4 2 7mm〇l)及（7)所得（3 25mg， 0.425mmol )溶在 C H 2 C12 ( 7 · 5 mL )，加入分子篩 4A ( 630mg ) ，AgOTf ( 125mg，0.486mmol )及 TM S OTf ( 20mg， 0.090mmol)，於氮氣及室温攪拌過夜。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮，進行矽膠層析純化。溶離以乙酸乙酯，再溶離以含5% MeOH之乙酸乙酯溶液，可得膠狀之目的化合物（410mg，產率 67%)。 IR vmax(膜）3500-3250，2926，2856，1746，1 547，1464 cnT1· 400 MHz lU NMR (CDC13) δ 0.88 (9H, t, J = 6.6 Hz), 1.26 (51H, bs), 1.38- 1.77 (8H, m), 2.72 (1H, bs, OH), 3.13 (1H, bs，OH)，3·2 卜3.90 (24H，m，含 2 個 3H，s，at 3.28 and 3.39 ppm), 4.07-4.30 (4H, m), 4.53-4.60 (8H, m), 4.65-4.90 (3H, m), 4.95 (1H, d, J = 3.7 Hz), 5.24-5.40 (8H, m), 5.89-5.99 (4H, m), 6.40 (1H,寬，NH)· (9) 2 — [(二烯丙膦酸基）氧基]乙基 6 — 0—〔2—去氧一 4— 0—二烯丙膦酸基一3 - 0—〔（R) — 3—甲氧癸基〕一 6— 0—甲基一 2—〔（Z) — 11—（十八碳燦醯基）胺基〕—β - D —吡喃葡糖基〕—3 - 0-十二基一 2— 0 - [(R) -109 - 200413400 —3 -羥基十四基]—oc—D—吡喃葡糖苷（第Cb2工程）將含（8)所得化合物（410mg，0.284mm〇l)之 THF — Ac 〇H ( 3 : 2, 15mL)溶液中加入鋅粉末（390mg)，於室温下攪拌4小時。將反應液過濾後，在室温濃縮，以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，將所得一級胺溶在T H F ( 3mL )。加入含重碳酸鈉（l〇〇mg)之水（0.9mL)及順-瓦克岑寧酸之醯氯（l〇2mg，0.340mmol)之 T H F ( 1.5mL)溶液，於室温劇烈攪拌2小時。反應液以乙酸乙酯稀釋，以重碳酸 φ 鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以乙酸乙酯，再溶離以含5 %MeOH in ethyl acetate gave the title compound as a wax (340 mg, yield 84%). IR vmax (film) 3388, (wide), 29 1 8, 2850, 1467 cnT1 · 400 MHz] H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 # (36H, bs), 1.4 Bu 1.73 (6H, m), 2.56 (1H, m, OH), 2.68 (1H, d, J = 2.9 Hz, OH), 3.12 (1H, bs, OH), 3.29 (1H, m), 3 44_ 3.92 (12H, m), 4.22-4.28 (2H, m), 4.55-4.59 (4H, m), 5.00 (1H, d, J = 3.7 Hz), 5.25-5.28 (2H, m), 5.35 -5 · 41 (2H, m, 5.90-6.00 (2H, m). (8) 2 — [(Diallylphosphono) oxy] ethyl 6—O— [2 —Deoxy-4—0 —Diallylphosphonic acid group 3—O — [(R) —3-methoxydecyl] —108—200413400 6—10—methyl-1 — [(trichloroethoxycarbonyl) amino] — β—D—pyranoglucosyl] —3—O—dodecyl—2—O — [(R) — 3-hydroxytetradecyl] —a—D-pyranoglucosamine (brother C b 1 Project) Trichloromethyliminofluorenyl 2-deoxy-4-10-diallylphosphonic acid group — 3 — 0 — [(R) — 3 —methoxydecyl] — 6 — 0 -Α, β-D-glucopyranoside (360 mg, 0.4 2 7 mm) and (7) (3 25mg, 0.425mmol) was dissolved in CH2C12 (7.5mL), and molecular sieves 4A (630mg), AgOTf (125mg, 0.486mmol) and TMS OTf (20mg, 0.090mmol) were added, and the mixture was stirred overnight at nitrogen and room temperature. Reaction The solution was diluted with ethyl acetate, washed with sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated, and purified by silica gel chromatography. Ethyl acetate was used, and then 5% MeOH in ethyl acetate was used to separate it. Solution to obtain the compound of interest (410 mg, yield 67%). IR vmax (film) 3500-3250, 2926, 2856, 1746, 1 547, 1464 cnT1 · 400 MHz lU NMR (CDC13) δ 0.88 (9H , t, J = 6.6 Hz), 1.26 (51H, bs), 1.38- 1.77 (8H, m), 2.72 (1H, bs, OH), 3.13 (1H, bs, OH), 3.2 · 3.90 (24H , M, including two 3H, s, at 3.28 and 3.39 ppm), 4.07-4.30 (4H, m), 4.53-4.60 (8H, m), 4.65-4.90 (3H, m), 4.95 (1H, d, J = 3.7 Hz), 5.24-5.40 (8H, m), 5.89-5.99 (4H, m), 6.40 (1H, wide, NH) · (9) 2 — [(diallylphosphonic acid) oxy] Ethyl 6 — 0 — [2 —deoxy — 4 — 0 — diallylphosphonic acid — 3 — 0 — [(R) — 3 —methoxydecane Group] 6-0-methyl-2 2-[(Z) -11- (octadecylfluorenyl) amino] -β-D-glucopyranosyl] -3-0-dodecyl-1 2-0-[(R) -109-200413400 —3 -hydroxytetradecyl] -oc-D-glucopyranoside (Project Cb2) will contain the compound obtained in (8) (410mg, 0.284mm0l) Zinc powder (390 mg) was added to a solution of THF-AcOH (3: 2, 15 mL), and the mixture was stirred at room temperature for 4 hours. The reaction solution was filtered, concentrated at room temperature, diluted with ethyl acetate, washed with a sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. The solution was concentrated by filtration, and the resulting primary amine was dissolved in THF (3 mL). A solution of sodium bicarbonate (100 mg) in water (0.9 mL) and a solution of cis-wakenamic acid in chloroform (102 mg, 0.340 mmol) in THF (1.5 mL) were added, and the mixture was stirred vigorously at room temperature for 2 hours. . The reaction solution was diluted with ethyl acetate, washed with a solution of sodium bicarbonate φ and saturated brine, and dried over magnesium sulfate. It was concentrated by filtration and purified by silica gel chromatography. Dissolve with ethyl acetate, then dissolve with 5%

MeOH之乙酸乙酯溶液，可得膠狀之標題化合物（3 55mg，產率82% )。 IR vmax(膜）3 3 9 8 (寬），2925, 2855，2480-2345 (w)，1640， 1 555，1465 cm'1. 400 MHz !H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (68H，bs)，1.40-1.79 ( 10H，m)，1.99-2.04 (4H, m)，2.17- · 2.21 (2H，m)，3.18 (1H，bs，OH)，3.27-3.95 (26H，m，含 2 個 3 Η, s, at 3.28 and 3.38 ppm), 4.07-4.27 (4H, m), 4.55-4.65 (8H, m)? 4.94 (1H, d, J = 3.7 Hz), 5.13 (1H, d, J = 8.1 Hz), 5.25 -5.3 9 ( 1 0H, m), 5.90-5.99 (4H, m)5 6.5 8 ( 1 H, d, J = 7.3 Hz, NH)· (10) 2—(膦酸氧基）乙基6—0—〔2 —去氧一 4一0-鱗酸基一 3— Ο—〔（R) — 3—甲氧癸基〕一 6— Ο—甲基一 -110 - 200413400 2—〔（Z) — 11一（十八碳烯醯基）胺基〕一 β - D —吡喃葡糖基〕—3— Ο-十二基一 2— Ο - [(R) - 3 —羥基十四基]一 α— D—吡喃葡糖苷（第Cb3工程）將（9)所得化合物（166 mg，0.109 mmol)溶在無水 THF ( lOmL )，力口入 E13 N ( 6 0 m g，0 · 5 9 3 m mo 1 ) ，HCOOH (5 6 mg , 1.216mmol)及 P d (PPh3) 4 ( 1 5 mg，0.09 6 mmo 1 )，於氮氣及54°C攪拌20小時。將反應液過濾濃縮，以 DEAE-纖維素8g之柱精製。溶離以CHCl3-Me0H-H20 (2:3: 1)之〇.〇5mol/L AcCTNH4溶液可得含目的物之部份。收集部份與CHCl3-Me0H-H20 (1:1:1)之混合物，加入 CHC13及0.15m〇l/L鹽酸水，於分液漏斗中攪拌，收集下層 CHC13層並濃縮，可得蠟狀之標題化合物（100mg，產率 67% )。 IR Vmax (KBr) 3289 (br), 2924, 2853, 1629 cm*1. 400 MHz lU NMR (C D C13 + C D 3 〇 D) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (68H, br s), 1.39- 1.75 ( 10H, m), 1.40- 1.77 (10H, m), 1.98-2.04 (4H, m), 2.17-2.22 (2H, m), 3.23-4.85 (26H, m,含 2 個 3H，s at 3.30 and 3.40 ppm)，4.00-4.18 (4H，m)， 4.69 (1H，d，J = 8.1 Hz)，4·94 (1H，d，J = 3.7 Hz)，5.33-5.38 (2H, m). C7〇H137N02〇P2 + H20 分析計算値：c，60.36; H，10.06; N， 1.01; P, 4.45 〇實測値：C，60.11; H，10.15; N，1.28; P， 4.34. 〔實施例6〕 -Ill - 2-（膦酸氧基）乙基 6 — 0—〔2-去氧—4— 0-膦酸基一 3 — 0—〔（R) — 3 —甲氧癸基〕一6— 0—甲基一2 — 〔（Z) - 11 一（十八碳烯醯基）胺基〕—β— D —吡喃葡糖基〕—3-0-十二基—2— Ο —十四基一 α - D —吡喃葡糖苷 (1) 烯丙基3— 0 —十二基—4，6— 0 —亞異丙基—2-〇-十四基一 α-D—吡喃葡糖苷（第Aa4工程）將實施例5 ( 3 )所得化合物（2.84g，6.63mmol )及1 —( 甲磺醯氧基）十四烷（2.33g，7.95mmol )溶在DMF ( 20mL )，加入氫化鈉（55%油中，347mg，7.59mmol )。將反應液於室温攪拌過夜，於冰冷却下加入甲醇以分解氫化鈉，以乙酸乙酯稀釋。以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以環己烷-乙酸乙酯（9 : 1 )，可得油狀標題化合物（3.10g，產率75% ) 〇 400 MHz lU NMR (CDC13) δ 0.88 (6Η, t5 J = 6.6 Hz), 1.26 (40H，broad s)，1.41 (3H, s)，1.48 (3H，s)，1.50-1.61 (4H, m), 3.30 (1H, m), 3.50-3.74 (8H, m), 3.84 (1H, m), 4.07 (1H, dd, J = 6.6, 13.2 Hz), 4.18 (1 H，d d，J 二 5 · 1，13.2 Hz), 4.91 (1H, d, J = 3.7 Hz), 5.22 (1H, m), 5.32 (1H, m), 5.92 (1H，m)· C38H7206 分析計算値：C，73.03; H，11.61。實測値：C， 73.02; H, 11.54. (2) 2 —經乙基3 — 0-十一基—4，6— 0 —亞異丙基一 2 -112 - 200413400 一 0—十四基一 α— D—吡喃葡糖苷（第A bl工程）將（1 )所得化合物（250mg, 〇.400mm〇l )，依實施例5 (5) 之方法反應，可得油狀標題化合物（173mg,產率 69% )。 IR vmax(膜）3453 (寬），2925，2855，1466，1 380，1 370 cnT1. 400 MHz !H NMR (CDCIs) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (40H，bs)，1.40 (3H，s)，1.48 (3H, s), 1.51-1.57 (4H，m)， 3.01(1H，bs，OH)，3.31 (1H，dd，J = 4.4，8.8 Hz)，3.50-3.91 (13H，m)，4.89 (1H, d，J = 3.7 Hz). · (3) 2 — [(二烯丙膦酸基）氧基]乙基3— 0—十二基一 4，6— Ο —亞異丙基一 2— Ο —十四基—α—D—吡喃葡糖苷 (第A b 2工程）將（2)所得化合物（154mg, 0.245mmol)，依實施例5 (6) 之方法反應，可得油狀標題化合物（180mg，產率 9 3%)。 IR vmax(膜）2925，2855，1466 cm-1· 400 MHz lU NMR (CDC13) δ 0.88 (6H, t, J = 6.6-7.3 Hz), · 1.2 卜 1.30 (40H, m)，1.39 (3H, s)，1.47 (3H，s), 1.50-1.58 (4H, m), 3.29 (1H, dd, 1 = 3.7, 8.8 Hz), 3.51-3.88 (1 1H, m), 4.23-4.27 (2H, m), 4.56-4.59 (4H, m), 4.89 (1H, d, J = 3.7 Hz), 5.21-5.41 (4H, m), 5.91-6.00 (2H, m). FABMS (陽離子）m/z, 789 [M + H] +，811 [M + Na] + . HRFABMS C43H81O10PNa 計算値：8 1 1.5465。實測値： 8 1 1.5472. -113 - 200413400 (4) 2 — [(二烯丙膦酸基）氧基]乙基3 — Ο-十二基— 2— Ο—十四基一 α—D —吡喃葡糖苷（第Ab3工程）將（3 )所得化合物（161mg, 0.204mmol)，依實施例5 (7)之方法反應，可得鱲狀之標題化合物（148mg,產率 97% )。 IR vmax(膜）3409 (br)，2925, 2854, 2626 (br w)，1465 cm·1· 400 MHz lR NMR (CDC13) δ 0.88 (6H, t, 1 = 6.6 Hz), 1.26 (40H, bs), 1.54- 1.58 (4H, m), 3.27 (1H, dd, J = 3.7, 8.8 Hz), 3.41-3.91 (11H, m), 4.24-4.28 (2H, m), 4.48-4.59 (4H, m), 4.95 (1H, d, J = 3.7 Hz), 5.19-5.40 (4H, m), 5.90-6.00 (2H, m). FABMS (陽離子）m/z，749 [M + H] +，771 [M + Na] + . HRFABMS C40H78O10P 計算値：749.5332。實測値： 749.5341. (5) 2 — [(二烯丙膦酸基）氧基]乙基6—0—〔2-去氧— 4一〇—二烯丙膦酸基一 3 — 0—〔（R) — 3—甲氧癸基〕一 6—〇 —甲基一 2—〔（三氯乙氧羰基）胺基〕一 β—Ε)一吡喃葡糖基〕一 3—0--^二基—2— 〇-十四基一 α—D—吡喃葡糖苷（第Cbl工程）將（4 )所得化合物（1 27mg，0· 1 70mmol )，依實施例5 (8 )之方法反應，可得膠狀之標題化合物（152mg，產率 63% ) 〇 vmax(膜）3287 (br)，3083 (w)，2926，2854，1 746，1650 (w)，1 544，1460 cm'1. -114 - 200413400 400 MHz JH NMR (CDC13) δ 0.88 (9H, t5 J = 6.6 Hz), 1.26 (52H, bs), 1.38- 1.46 (2H, m), 1.5 3- 1.5 8 (4H, m), 1.69-1.77 (2H, ni)，2.65 (1H，bs, OH)，3.2 1 -3.89 (23H，m，含 2 個 3H， s at 3.28 and 3.39 ppm), 4.09-4.32 (4H, m), 4.52-4.60 (8H, m), 4.90 (1H, d, 1 = 3.1 Hz), 5.24-5.40 (8H, m)? 5.89-5.99 (4H, m), 6.41 (1H, bs, NH). FABMS (陽離子）m/z，1452，1450 [M + Na] + · HRFABMS C67Hi22N〇2〇P2Na g十算値· 1450·6999。貫測値· 1450.6974. (6) 2 — [(二烯丙膦酸基）氧基]乙基6 — Ο—〔2—去氧一 4 一 0-二烯丙膦酸基—3— 0—〔（R) — 3 —甲氧癸基〕— 6—0-甲基一 2 —〔（Ζ) — 11—（十八碳烯醯基）胺基〕 —β—D -吡喃葡糖基〕—3— 0 —十二基—2— Ο —十四基一 α — D—吡喃葡糖苷（第Cb2工程）將（5 )所得化合物（322mg，0.225mmol )，依實施例5 (9)之方法反應，可得膠狀之標題化合物（188mg，產率 55% )。 IR vmax(膜）3299 (br w)，3 08 5 (w)，2925，2855, 1 65 6, 1 550, 1 465 cm-1· 400 MHz NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (70H，bs)，1.40-1.7 9(10H，m)，1.99-2.07 (4H，m)，2.17-2.25 (2H, m), 3.01 (1H, d, J = 2.9 Hz, OH), 3.1 7-3.82 (24H, m，含 2 個 3H，s at 3.28 and 3·38 ppm), 3.97-4.31 (5H，m)， 4.52-4.58 (8H, m), 4.88 (1H, d, J = 3.7 Hz), 5.13 (1H, d, -115 - 200413400 J = 8. 1 Hz), 5.23-5.41 (10H? m), 5.89-6.00 (4H, m), 6.62 (1H, d，J = 6.6 Hz，NH). FABMS (陽離子）m/z，1 540 [M + Na] + . HRFABMSC82H153N〇19P2Na 計算値：1541.0410。實測値： 1541.0365. (7) 2—（膦酸氧基）乙基6—0—〔2 —去氧—4— Ο — 膦酸基一3— Ο—〔（R) — 3—甲氧癸基〕一 6 — Ο —甲基一 2—〔（Ζ) — 11一（十八碳烯醯基）胺基〕一 β— D —吡喃葡糖基〕一 3— 0 —十二基一 2 — Ο —十四基—a— D —吡喃葡籲糖苷（第C b 3工程）將（6)所得化合物（172mg，0.113mmol)，依實施例5 (10)之方法反應，可得蠟狀之標題化合物（52mg，產率 34% )。 IR vmax (KBr) 3 299 (br w)，3085 (w)，2925，2855，1 656, 1 550, 1 465 cm"1. 400 MHz ιΉ NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (70H，bs)，1.40- 1.79 ( 10H, m)，1.99-2.07 (4H，m)，2.17- · 2.25 (2H，m)，3.01 (1H，d，J = 2.9 Hz，〇H)，3.1 7-3.82 (24H， m，含 2 個 3H，s at 3.28 and 3.38 ppm)，3.97-4.31 (5H，m)， 4.52-4.5 8 (8H, m), 4.88 (1H, d, J = 3.7 Hz), 5.13 (1H, d9 J = 8.1 Hz), 5.23-5.41 (10H, m), 5.89-6.00 (4H, m), 6.62 (1H, d, J = 6.6 Hz, NH). FABMS (陰離子）m/z，1 356 [Μ-ΗΓ，1 378 [M + Na-2H]·. HRFABMS C7〇H136N019P2Na 計算値：1 3 5 6.9 1 82。實測値： -116 - 200413400 1356.9155. C70H137N〇19P2,2.5xCH3COONH4 分析計算値：C，58·06; H， 10.04; Ν，3· 1 6; Ρ，3·99。實測値：C，5 8 · 0 8 ; Η，9 · 2 6 ; Ν， 2.81; Ρ? 3.74. 〔實施例7〕 2 —膦酸乙基6 —〇一[2—去氧一3 —〇一{(R) — 3 —甲氧癸基丨一 6 —〇一甲基一 2—〔（Z) — 11 —十八碳烯醯胺基〕—4 一〇—膦酸基—β— D —吡喃葡糖基]—2，3—二一〇—十二基一α— D —吡喃葡糖苷 (1) 2 —溴乙基2，3 —二一〇一十二基一4，6—〇一亞異丙基一 a— D—吡喃葡糖苷（第D a 1工程）將2 —羥乙基2，3 —二一〇一十二基一 4，6—〇一亞異丙基一a— D —吡喃葡糖苷（1.10g，1.83mmol)溶在二氯甲烷（10mL)，力□入四溴化碳（731 mg，2.20 mmol )及三苯膦（67 1mg，2.5 6mm〇l)，於室温下攪拌2小時。將反應液以二氯甲烷稀釋，以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化，溶離以己烷一乙馨酸乙酯（9 : 1)，可得標題化合物（1.20g，產率99%)。 IR vmax(CHCl3) 2927, 2855 cm'1 · 500 MHz 4 NMR (CDC13) δ 0·88 (6H，t，J = 6.8 Hz)，1.25-1·60 (46H，m，含 3H，s，δ 1.41，3H，s, δ 1.48)，3.30 (1H，dd, J = 2.9, 8.8 Hz), 3.50-3.57 (4H, m), 3.59-3.75 (6H, m), 3.83-3·96 (3H，m)，4.91 (1H，d，J = 3.9 Hz). MS (FAB,陽性）m/z 701 (M + K) +，6 8 5 (M + Na) + . -117 - 200413400 HRMS (ESI，陽性），計算値 C35H67Br06Na: 685.4002 ;實測値：685.405 6. (2 ) 2 —（二烯丙膦酸基）乙基2，3 —二一〇—十二基一 α — D —吡喃葡糖苷（第D a 2工程及第D a 3工程）將（1)所得化合物（1.20g，1.8 1 mmol)加入亞磷酸三烯丙酯（5mL)，於氮氣下及180°C下加熱攪拌2小時，減壓濃縮，以矽膠柱層析純化，溶離以己烷一乙酸乙酯（2 : 3 )可得混合物。將混合物溶在80%乙酸水溶液，於60 °C下攪拌1小時，減壓濃縮，以乙酸乙酯稀釋。以水，飽和碳酸氫鈉水溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化，溶離以氯仿-乙醇（20 : 1 )，可得標題化合物（ 760mg，產率60%)。 IR vmax(CHCl3) 3 598, 3420, 3089, 2927，2855 cm-1 · 500 MHz NMR (CDC13) δ 0.88 (6H, t, J = 6.8 Hz), 1.26- 1.61 (40 H，m)，2.28(1H，brs，〇H)，2.58 (1H，brs，〇H)， 3.27 ( 1H, dd, J = 2.9，9.8 Hz), 3.44-3.53 (3 H ^ m), 3.57- 3.62 (2H，m)，3.70-3.80 (3H，m), 3.84-3.92 (2H，m)，3·98 (1H, m), 4.51-4.60 (4H, m), 4.90 (1H, d, J = 2.9 Hz), 5.24-5.38 (4H, m), 5.90-5.98 (2H, m). MS (FAB,陽性）m/z 743 (M + K) + , 727 (M + Na) + . HRMS (ESI,陽性），計算値 C38H7 3 09PNa: 727.4889 ;實測値：727.4892. (3 ) 2 — （二烯丙膦酸基）乙基6 —〇一 [2 —去氧一4 — 〇一二烯丙膦酸基一 3 —〇一〔（R ) — 3 —甲氧癸基〕—6 -118- 200413400 —〇一甲基一2— （ 2,2,2—三氯乙氧羰胺基）一 β— D —吡喃葡糖基]一二一〇一十二基一 α — D -吡喃葡糖苷（第D b 1工程）將三氯甲基亞胺醯基2 —去氧一 4 一〇一二烯丙膦酸基一 3 —〇一〔(R ) — 3 —甲氧癸基〕一6 —〇一甲基一α，β — D —卩比喃葡糖苷（ 338mg, 0.401 mmol)溶在二氯甲院（ 5mL)，加入（2)所得化合物（189mg, 0.268m mol)，於氮氣下加入三氟甲擴酸銀（155mg, 0.604mmol)，於室温下攪拌1小時。反應液中加入飽和碳酸氫鈉水溶液以中止反應，以二氯甲烷萃取，以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化，溶離以己烷一乙酸乙酯（1 : 9 )，可得標題化合物（27 3 mg，產率 74% )。 IR vmax(CHCl3) 3449，325 5，308 8，2928，2873，2 8 5 6, 1 7 34 cm"1. 500 MHz NMR (CDC13) δ 0.88 (9H, t, J = 6.8 Hz), 1.26-1.80 (54H, m), 2.24-2.32 (2H, m), 2.55 (1H, s, OH), 3.21-3.36 (7H，m，含 3H，s，δ 3.29), 3.39 (3H, s), 3.42-3.66 (7H， m)，3.71-3.88 (6H，m)，3.92-3.99 (2H，m)，4·16 (1H，d， J=10.7 Hz), 4.30 (1H, q，J = 8.8，9·8 Hz), 4.5 3 -4.59 (8H， m)，4.70，4.78 (2H, ABq，J=1 1.7 Hz), 4.87 (1H, d，J = 2.9 Hz)，4.93 (1H, d, J 二 7.8 Hz)，5.23-5.39 (8H，m)，5.88-5.98 (4H，m)，6.75 (1H，d，J = 6·8Ηζ，ΝΗ)· MS (FAB,陽性）m / z 1 4 _2 2 ( M + K) +，1 4 0 6 (M + N a ) 200413400 HRMS (ESI,陽性），計算値 C65Hi】8Cl3N〇19P2Na: 1406.6732;實測値：1406.6720. (4) 2—(二烯丙膦酸基）乙基6 —〇一 [2—去氧—4 — 〇一二烯丙膦酸基一 3 —〇一〔（R) — 3 —甲氧癸基〕—6 —〇一甲基一 2—〔（Z) — 11—十八碳燒酸胺基〕一β — D —毗喃葡糖基]—2，3 —二一〇一十二基—a— D —吡喃葡糖苷（第D b 2工程）將（3)所得化合物（22 0mg, 0.159mm〇l)溶在四氫呋喃 (4mL)，加入乙酸（0.5mL)及鋅（210mg)，於室温下攪拌3小時。濾除鋅後，將反應液減壓濃縮，以乙酸乙酯稀釋，以飽和碳酸氫鈉水溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑所得粗胺溶在二氯甲烷（5mL ) ’加入（Z ) — 11—十八碳嫌酸（68mg，0.239mmol)及 1 一乙基一3 —（3—二甲胺丙基）碳化二亞胺鹽酸鹽（55mg，〇.287 mmol)，於室温下攪拌20小時。將反應液以二氯甲烷稀釋，以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化，溶離以乙酸乙酯可得標題化合物（122mg，產率52% )。 IR vmax(CHCl3) 3 004, 2928, 2 8 5 6, 1 662 cm-1. 500 MHz !H NMR (CDC13) δ 0.88 (12H, t, J = 6.8 Hz), 1.25-1.80 (76H, m), 1.99-2.01 (4H, m), 2.16-2.33 (4H, m), 2.85 (1H, d，J = 3.9 Hz，〇H)，3.07 (1H，m)，3.23 - 3,2 5 (2H，m)， 3.29(3H，s)，3.36(lH，m)，3.38(3H，s)，3.44(lH，t，J：=8.8 H z )，3.4 8 - 3.8 4 ( 1 2 H，m)，3 · 9 1 ( 1 H，in )，4.09 (1H，t，J二9.8， -120 - 200413400 8.8 Hz)，3.48-3.84 ( 1 2H，m), 3·91 (1H，m)，4.09 (1H，t, J-9-8, 8.8 Hz), 4.17 ( 1 H, d，J=10.7 Hz)，4.25 (1H，q，卜9.8 8.8 Hz), 4.50-4.5 8 ( 8H，m)，4.85 (1H，d，J = 3.9 Hz), 5.19 (1H，d，J二7.8 Hz), 5.23-5.38 (10H，m), 5.89-5.9 8 (4H? m), 6.91 (1H, d, J = 6.8 Hz, NH). MS (FAB，陽性）m/z 1512 (M + K) + , 1 496 (M + Na) + · HRMS (ESI,陽性），計算値 C80H149N〇18P2Na: 1 497.0 1 39 ;實測値：1 4 9 7.0 1 2 3 . (5) 2—麟酸乙基6 —〇一[2—去氧一3—〇一〔（r) —3—甲氧癸基〕一6 —〇一甲基一2- 〔（Z) — 11—十八碳烯醯胺基〕一 4 一 ◦一膦酸基一 β— D -吡喃葡糖基]一 2 ’ 3—二一〇一十二基一 a—D — □比喃葡糖苷（第Db3工程）將（4 )所得化合物（1 1 〇 m g，0 · 0 7 5 m m ο 1 )溶在四氫呋喃 (5mL)，加入三苯膦（9.8mg，0.037mmol)，三乙胺（ 52pL，0.373mmol )，甲酸（2 8 pL，0 · 7 4 2 m m ο 1 )及肆三苯膦鈀（4.4mg，0.004mmol )，於5 0 °C攪拌5小時。將反應液減壓濃縮’以仿稀釋，以0.1 m ο 1 / L鹽酸水溶液洗浄，將氯仿層減壓濃縮。所得混合物以D E A E纖維素（乙酸型 )柱層析精製，溶離以0.0 5 mo 1/L乙酸銨溶液（氯仿：甲醇：水=2 : 3 : 1 )。溶在氯仿（4mL )，甲醇（8mL )及 0. lmol/L鹽酸水溶液（3.2mL )，加入氯仿（4mL )及 0.1mol/L鹽酸水溶液（4mL)並洗浄。分離氯仿層，減壓蒸除溶劑，可得白色固體之標題化合物（80 m g ,產率8 2 % -121 - 200413400 j ° IR vmax(KBr) 3284， 3218， 3178， 3116， 2955, 2924， 2853， 1655，1 6 3 0 cm-1. 500 MHz ]H NMR ( C D 3 〇 D : C D C 13 = 5:1) δ 0.90 (12H, t, J = 6.8 Hz), 1.28 - 1.67 (74H，m)，1.7 3 - 1.77 (2H, m), 2.01-2.03 (4H, m), 2.16 (2H, dt, J = 7.8, 18.6 Hz), 2.25 (2H, t, J = 6.8 Hz), 3.22 (1H，dd，J = 2.9，9.8 Hz), 3.31 (3H, s), 3.34 (lH，m)，3.41(3H，s)，3.46(lH，t,J = 9.8，8.8Hz)，3.54-3.85 (15H，m)，3.96 (1H，m)，4.07-4.12 (2H, m), 4.54 (1H， d, J = 8.8 Hz). 4.87 (1H, d, J = 3.9 Hz), 5.31-5.37 (2H, m). 〔實施例8〕膦酸基6—〇一 {2 —去氧一 3 — Ο—〔（R) — 3—甲氧癸基〕一 6— Ο—甲基一 2—〔（Z) — 11 一（十八碳烯醯基）胺基〕一 4一 Ο-膦酸基一 β-D-吡喃葡糖基}一3— 0-十二基一 2 — 0— [(R) - 3—羥基十四基]—a— D —吡喃葡糖苷 (1) 1，2: 5，6 —二—0 —亞異丙基—3 — 〇 —十二基一 ex — D -呋喃葡萄糖（第A a 1工程）將1，2: 5，6 —二一0 —亞異丙基一 a— D-呋喃葡萄糖 (2 6.0g，O.lOmol)及甲磺酸十二碳酯（13.2g，〇.〇5mol) ，依實施例1 ( 1 )之方法反應，可得油狀物之標題化合物 (3 1 . 1 g，產率 7 5 % )。 400 MHz ]H NMR (CDC13) δ 0.88 (3H? t, J = 6.6 Hz), 1.26 (18H，bs)，1.32 (3H，s)，1.35 (3H，s)，1.43 (3H，s)，1.50 (3 H，s )，1 . 5 2 - 1 . 5 7 (2 H，m)，3.5 1 ( 1 H，m )，3 , 5 9 ( 1 H，m )， -122 - 200413400 3.85 (1H，d，J = 2.9 Hz), 3.98 (1H，m)，4.0 6-4 izi * 14 (3H, m)5 4.31 (1H，m)，4.52 (1H，d，J 二3.7 Hz)，5.88 , UH，d, J:3 7A solution of MeOH in ethyl acetate gave the title compound as a gel (3 55 mg, 82% yield). IR vmax (film) 3 3 9 8 (width), 2925, 2855, 2480-2345 (w), 1640, 1 555, 1465 cm'1. 400 MHz! H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (68H, bs), 1.40-1.79 (10H, m), 1.99-2.04 (4H, m), 2.17- · 2.21 (2H, m), 3.18 (1H, bs, OH), 3.27 -3.95 (26H, m, including 2 3 Η, s, at 3.28 and 3.38 ppm), 4.07-4.27 (4H, m), 4.55-4.65 (8H, m)? 4.94 (1H, d, J = 3.7 Hz ), 5.13 (1H, d, J = 8.1 Hz), 5.25 -5.3 9 (1 0H, m), 5.90-5.99 (4H, m) 5 6.5 8 (1 H, d, J = 7.3 Hz, NH) (10) 2- (phosphonooxy) ethyl 6-0— [2 —deoxy-4—0—phosphonic acid—3—O — [(R) —3-methoxydecyl] —6— Ο-methyl-110-200413400 2 — [(Z) — 11- (octadecenyl) amino] -β-D-glucopyranosyl] -3—O-dodecyl-2 — Ο-[(R)-3 -hydroxytetradecyl] -α-D-glucopyranoside (Project Cb3) The compound (166 mg, 0.109 mmol) obtained in (9) was dissolved in anhydrous THF (10 mL), E13 N (60 mg, 0.59 3 m mo 1), HCOOH (56 mg, 1.216 mmol) and P d (P Ph3) 4 (15 mg, 0.09 6 mmo 1), and stirred under nitrogen at 54 ° C for 20 hours. The reaction solution was filtered and concentrated, and purified by a DEAE-cellulose 8g column. Dissolve in 0.05ml / L AcCTNH4 solution of CHCl3-Me0H-H20 (2: 3: 1) to obtain the part containing the target. Collect the mixture of the part and CHCl3-Me0H-H20 (1: 1: 1), add CHC13 and 0.15 ml / L hydrochloric acid water, stir in a separatory funnel, collect the lower CHC13 layer and concentrate to obtain a waxy The title compound (100 mg, 67% yield). IR Vmax (KBr) 3289 (br), 2924, 2853, 1629 cm * 1. 400 MHz lU NMR (CD C13 + CD 3 〇D) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (68H, br s), 1.39- 1.75 (10H, m), 1.40- 1.77 (10H, m), 1.98-2.04 (4H, m), 2.17-2.22 (2H, m), 3.23-4.85 (26H, m, including 2 3H, s at 3.30 and 3.40 ppm), 4.00-4.18 (4H, m), 4.69 (1H, d, J = 8.1 Hz), 4.94 (1H, d, J = 3.7 Hz), 5.33-5.38 (2H , m). C7〇H137N02〇P2 + H20 Analytical calculation 値: c, 60.36; H, 10.06; N, 1.01; P, 4.45 〇 Measured 値: C, 60.11; H, 10.15; N, 1.28; P, 4.34. [Example 6] -Ill-2- (phosphonooxy) ethyl 6-0- [2-deoxy-4-0-phosphono-3-0-[(R) -3-methoxydecane Yl] -6-0-methyl-2 — [(Z)-11 mono (octadecenyl) amino] -β-D-glucopyranosyl] -3-0-dodecyl— 2-0-tetradecyl-α-D-glucopyranoside (1) allyl 3--0-dodecyl-4,6--0-isopropylidene-2- 2-tetradecyl-α -D-glucopyranoside (Project Aa4) The compound obtained in Example 5 (3) (2. 84 g, 6.63 mmol) and 1- (methanesulfonyloxy) tetradecane (2.33 g, 7.95 mmol) were dissolved in DMF (20 mL), and sodium hydride (55% oil, 347 mg, 7.59 mmol) was added. The reaction solution was stirred at room temperature overnight, and methanol was added under ice-cooling to decompose sodium hydride, and diluted with ethyl acetate. Wash with water and saturated saline, and dry under magnesium sulfate. It was concentrated by filtration and purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (9: 1) to obtain the title compound (3.10 g, yield 75%). 〇400 MHz 1U NMR (CDC13) δ 0.88 (68, t5 J = 6.6 Hz), 1.26 (40H, broad s), 1.41 (3H, s), 1.48 (3H, s), 1.50-1.61 (4H, m), 3.30 (1H, m), 3.50-3.74 (8H, m), 3.84 (1H , m), 4.07 (1H, dd, J = 6.6, 13.2 Hz), 4.18 (1 H, dd, J 2 5 · 1, 13.2 Hz), 4.91 (1H, d, J = 3.7 Hz), 5.22 (1H , m), 5.32 (1H, m), 5.92 (1H, m) · C38H7206 Analytical calculation 値: C, 73.03; H, 11.61. Measured fluorene: C, 73.02; H, 11.54. (2) 2 —Ethyl 3 — 0-undecyl — 4, 6 — 0 —isopropylidene — 2 — 112 — 200413400 — 0 — tetradecyl — 1 α-D-glucopyranoside (Project A bl) The compound (250 mg, 0.400 mm) obtained in (1) was reacted according to the method of Example 5 (5) to obtain the title compound (173 mg, Yield 69%). IR vmax (film) 3453 (wide), 2925, 2855, 1466, 1 380, 1 370 cnT1. 400 MHz! H NMR (CDCIs) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (40H, bs) , 1.40 (3H, s), 1.48 (3H, s), 1.51-1.57 (4H, m), 3.01 (1H, bs, OH), 3.31 (1H, dd, J = 4.4, 8.8 Hz), 3.50-3.91 (13H, m), 4.89 (1H, d, J = 3.7 Hz). · (3) 2 — [(Diallylphosphono) oxy] ethyl 3-0—dodecyl-4,6— 〇—Isopropylidene-2— 0—tetradecyl—α-D-glucopyranoside (Project A b 2) The compound (2) obtained in (2) (154 mg, 0.245 mmol) was used according to Example 5 (6) Reaction in this way gave the title compound (180 mg, yield 93%) as an oil. IR vmax (film) 2925, 2855, 1466 cm-1 · 400 MHz lU NMR (CDC13) δ 0.88 (6H, t, J = 6.6-7.3 Hz), · 1.2 bu 1.30 (40H, m), 1.39 (3H, s), 1.47 (3H, s), 1.50-1.58 (4H, m), 3.29 (1H, dd, 1 = 3.7, 8.8 Hz), 3.51-3.88 (1 1H, m), 4.23-4.27 (2H, m ), 4.56-4.59 (4H, m), 4.89 (1H, d, J = 3.7 Hz), 5.21-5.41 (4H, m), 5.91-6.00 (2H, m). FABMS (cation) m / z, 789 [M + H] +, 811 [M + Na] +. HRFABMS C43H81O10PNa Calculated 値: 8 1 1.5465. Found 値: 8 1 1.5472. -113-200413400 (4) 2 — [(Diallylphosphono) oxy] ethyl 3 — 0-dodecyl — 2 — 0 —tetradecyl α — D — Pyranoglucoside (Project Ab3) The compound (161 mg, 0.204 mmol) obtained in (3) was reacted according to the method of Example 5 (7) to obtain the title compound (148 mg, yield 97%) in the form of a maggot. IR vmax (film) 3409 (br), 2925, 2854, 2626 (br w), 1465 cm · 400 MHz lR NMR (CDC13) δ 0.88 (6H, t, 1 = 6.6 Hz), 1.26 (40H, bs ), 1.54- 1.58 (4H, m), 3.27 (1H, dd, J = 3.7, 8.8 Hz), 3.41-3.91 (11H, m), 4.24-4.28 (2H, m), 4.48-4.59 (4H, m ), 4.95 (1H, d, J = 3.7 Hz), 5.19-5.40 (4H, m), 5.90-6.00 (2H, m). FABMS (cation) m / z, 749 [M + H] +, 771 [ M + Na] +. HRFABMS C40H78O10P Calculated 値: 749.5332. Found 値: 749.5341. (5) 2 — [(Diallylphosphonic acid) oxy] ethyl 6-0— [2-deoxy-4—0—diallylphosphonic acid 3—0— [ (R) — 3-methoxydecyl] -6-O-methyl-2 — [(trichloroethoxycarbonyl) amino] -β-E) -glucopyranosyl] -3-0— ^ Diyl-2-O-tetradecyl-α-D-glucopyranoside (Cbl project) The compound obtained in (4) (127 mg, 0.170 mmol) was used according to the method of Example 5 (8) The title compound (152 mg, yield 63%) was obtained as a gel. OVmax (membrane) 3287 (br), 3083 (w), 2926, 2854, 1 746, 1650 (w), 1 544, 1460 cm ' 1. -114-200413400 400 MHz JH NMR (CDC13) δ 0.88 (9H, t5 J = 6.6 Hz), 1.26 (52H, bs), 1.38- 1.46 (2H, m), 1.5 3- 1.5 8 (4H, m ), 1.69-1.77 (2H, ni), 2.65 (1H, bs, OH), 3.2 1 -3.89 (23H, m, including 2 3H, s at 3.28 and 3.39 ppm), 4.09-4.32 (4H, m) , 4.52-4.60 (8H, m), 4.90 (1H, d, 1 = 3.1 Hz), 5.24-5.40 (8H, m)? 5.89-5.99 (4H, m), 6.41 (1H, bs, NH). FABMS (Cation) m / z, 1452, 1450 [M + Na] + · HRFABMS C67Hi22NO2P2Na g ten counts · 1450 · 6999. (6) 2 — [(diallylphosphonic acid) oxy] ethyl 6 — 0— [2—deoxy-4—0—diallylphosphonic acid —3— 0— [(R) — 3-methoxydecyl] — 6-0-methyl-1 — [(Z) — 11 — (octadecenyl) amino] —β-D-glucopyranosyl ] —3—0—Dodecyl—2—O—tetradecyl—α—D—glucopyranoside (Cb2 project) The compound (5) obtained in (5) (322 mg, 0.225 mmol) was used according to Example 5 (9 ) Method to give the title compound (188 mg, yield 55%) as a gel. IR vmax (film) 3299 (br w), 3 08 5 (w), 2925, 2855, 1 65 6, 1 550, 1 465 cm-1 · 400 MHz NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (70H, bs), 1.40-1.79 (10H, m), 1.99-2.07 (4H, m), 2.17-2.25 (2H, m), 3.01 (1H, d, J = 2.9 Hz, OH), 3.1 7-3.82 (24H, m, including 2 3H, s at 3.28 and 3.38 ppm), 3.97-4.31 (5H, m), 4.52-4.58 (8H, m), 4.88 (1H, d , J = 3.7 Hz), 5.13 (1H, d, -115-200413400 J = 8. 1 Hz), 5.23-5.41 (10H? M), 5.89-6.00 (4H, m), 6.62 (1H, d, J = 6.6 Hz, NH). FABMS (cation) m / z, 1 540 [M + Na] +. HRFABMSC82H153N〇19P2Na Calculated 値: 1541.0410. Measured rhenium: 1541.0365. (7) 2- (phosphonooxy) ethyl 6-0— [2 —deoxy-4 — 0 —phosphonic acid group 3 — 0 — [(R) — 3 —methoxydecane Yl] -6-O-methyl-2 — [(Z) —11- (octadecenyl) amino] -β-D-glucopyranosyl] -3-0-dodecyl-1 2—O—tetradecyl—a—D—glucopyranoside (Project C b 3) The compound (172 mg, 0.113 mmol) obtained in (6) can be reacted according to the method of Example 5 (10) to obtain The title compound was obtained as a wax (52 mg, 34% yield). IR vmax (KBr) 3 299 (br w), 3085 (w), 2925, 2855, 1 656, 1 550, 1 465 cm " 1. 400 MHz ιΉ NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (70H, bs), 1.40- 1.79 (10H, m), 1.99-2.07 (4H, m), 2.17- · 2.25 (2H, m), 3.01 (1H, d, J = 2.9 Hz, 〇 H), 3.1 7-3.82 (24H, m, including 2 3H, s at 3.28 and 3.38 ppm), 3.97-4.31 (5H, m), 4.52-4.5 8 (8H, m), 4.88 (1H, d, J = 3.7 Hz), 5.13 (1H, d9 J = 8.1 Hz), 5.23-5.41 (10H, m), 5.89-6.00 (4H, m), 6.62 (1H, d, J = 6.6 Hz, NH) .FABMS (Anion) m / z, 1 356 [M-ΗΓ, 1 378 [M + Na-2H] .. HRFABMS C70H136N019P2Na Calculated 値: 1 3 5 6.9 1 82. Measured 値: -116-200413400 1356.9155. C70H137N019P2, 2.5xCH3COONH4 Analytical calculation 値: C, 58 · 06; H, 10.04; N, 3. 16; P, 3.99. Measured fluorene: C, 5 8 · 0 8; hydrazone, 9 · 2 6; N, 2.81; P? 3.74. [Example 7] 2-phosphonic acid ethyl 6-〇-1 [2-deoxy-3 —〇 Mono {(R) — 3-methoxydecyl 丨 6 — 0 — methyl — 2 — [(Z) — 11 — octadecenylamino] 4 — 10 — phosphonic acid — β — D —Pyranoglucosyl] -2,3-dioxo-dodecyl-α-D-glucopyranoside (1) 2-bromoethyl 2,3-dioxoyl-12, 6-O-isopropylidene-a-D-glucopyranoside (Project D a 1) will be 2-hydroxyethyl 2,3-dioxoyl-12-yl-4,6--0-isopropylidene Propyl-a-D-glucopyranoside (1.10g, 1.83mmol) was dissolved in dichloromethane (10mL), and carbon tetrabromide (731 mg, 2.20 mmol) and triphenylphosphine (67 1mg, 2.5 6 mm), and stirred at room temperature for 2 hours. The reaction solution was diluted with dichloromethane, washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The title compound (1.20 g, yield 99%) was obtained by dissolving ethyl acetate (9: 1) in hexane monoacetate. IR vmax (CHCl3) 2927, 2855 cm'1 · 500 MHz 4 NMR (CDC13) δ 0 · 88 (6H, t, J = 6.8 Hz), 1.25-1 · 60 (46H, m, including 3H, s, δ 1.41, 3H, s, δ 1.48), 3.30 (1H, dd, J = 2.9, 8.8 Hz), 3.50-3.57 (4H, m), 3.59-3.75 (6H, m), 3.83-3 · 96 (3H, m), 4.91 (1H, d, J = 3.9 Hz). MS (FAB, positive) m / z 701 (M + K) +, 6 8 5 (M + Na) +. -117-200413400 HRMS (ESI, (Positive), calculated 値 C35H67Br06Na: 685.4002; found 685: 685.405 6. (2) 2- (diallylphosphonic acid) ethyl 2,3-dioxo-dodecyl-α-D-glucopyranoside (Project D a 2 and Project D a 3) Add the compound obtained in (1) (1.20 g, 1.8 1 mmol) to triallyl phosphite (5 mL), and heat and stir under nitrogen at 180 ° C for 2 hours , Concentrated under reduced pressure, purified by silica gel column chromatography, and dissolved in hexane-ethyl acetate (2: 3) to obtain a mixture. The mixture was dissolved in an 80% acetic acid aqueous solution, stirred at 60 ° C for 1 hour, concentrated under reduced pressure, and diluted with ethyl acetate. It was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The title compound (760 mg, yield 60%) was obtained by chloroform-ethanol (20: 1) separation. IR vmax (CHCl3) 3 598, 3420, 3089, 2927, 2855 cm-1 · 500 MHz NMR (CDC13) δ 0.88 (6H, t, J = 6.8 Hz), 1.26- 1.61 (40 H, m), 2.28 ( 1H, brs, 0H), 2.58 (1H, brs, 0H), 3.27 (1H, dd, J = 2.9, 9.8 Hz), 3.44-3.53 (3 H ^ m), 3.57- 3.62 (2H, m) , 3.70-3.80 (3H, m), 3.84-3.92 (2H, m), 3.98 (1H, m), 4.51-4.60 (4H, m), 4.90 (1H, d, J = 2.9 Hz), 5.24 -5.38 (4H, m), 5.90-5.98 (2H, m). MS (FAB, positive) m / z 743 (M + K) +, 727 (M + Na) +. HRMS (ESI, positive), calculated値 C38H7 3 09PNa: 727.4889; Measured 値: 727.4892. (3) 2 — (diallylphosphono) ethyl 6—〇— [2 —deoxy—4—〇—diallylphosphonic acid—3— 〇一 [(R) — 3-methoxydecyl] -6-118- 200413400 —〇-methyl-2— (2,2,2-trichloroethoxycarbonylamino) —β-D—pyran Glucosyl] 1210 12-yl-α-D-glucopyranoside (Project D b 1) Trichloromethyliminofluorenyl 2-deoxy-4 10-diallylphosphine Acid group 3-O-[(R) -3-methoxydecyl] -6-O-methyl α, β — D —pyranoglucoside (338mg, 0.401 mmol) was dissolved in dichloromethane (5mL), the compound obtained in (2) (189mg, 0.268m mol) was added, and trifluoromethane acid was added under nitrogen. Silver (155 mg, 0.604 mmol) was stirred at room temperature for 1 hour. A saturated sodium bicarbonate aqueous solution was added to the reaction solution to terminate the reaction, and the mixture was extracted with dichloromethane, washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography, and the solvent was separated with hexane-ethyl acetate (1: 9) to obtain the title compound (27 3 mg, yield 74%). IR vmax (CHCl3) 3449,325 5,308 8,2928,2873,2 8 5 6, 1 7 34 cm " 1. 500 MHz NMR (CDC13) δ 0.88 (9H, t, J = 6.8 Hz), 1.26- 1.80 (54H, m), 2.24-2.32 (2H, m), 2.55 (1H, s, OH), 3.21-3.36 (7H, m, including 3H, s, δ 3.29), 3.39 (3H, s), 3.42 -3.66 (7H, m), 3.71-3.88 (6H, m), 3.92-3.99 (2H, m), 4.16 (1H, d, J = 10.7 Hz), 4.30 (1H, q, J = 8.8, 9 · 8 Hz), 4.5 3 -4.59 (8H, m), 4.70, 4.78 (2H, ABq, J = 1 1.7 Hz), 4.87 (1H, d, J = 2.9 Hz), 4.93 (1H, d, J Two 7.8 Hz), 5.23-5.39 (8H, m), 5.88-5.98 (4H, m), 6.75 (1H, d, J = 6 · 8Ηζ, ΝΗ) · MS (FAB, positive) m / z 1 4 _2 2 (M + K) +, 1 4 0 6 (M + Na) 200413400 HRMS (ESI, positive), calculated 値 C65Hi] 8Cl3N〇19P2Na: 1406.6732; found 140: 1406.6720. (4) 2- (diallyl) Phosphonic acid group) Ethyl 6-0- [2-deoxy-4—〇-diallylphosphonic acid group 3—0 — [(R) —3-methoxydecyl] -6—O-methyl A 2-[(Z) — 11-octadecanoic acid amine group] — β — D —pyranoglucosyl] — 2, 3 — 210 -A-D-glucopyranoside (Project D b 2) The compound obtained in (3) (220 mg, 0.159 mm) was dissolved in tetrahydrofuran (4 mL), and acetic acid (0.5 mL) and zinc (210 mg) were added. And stirred at room temperature for 3 hours. After the zinc was removed by filtration, the reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with a saturated sodium bicarbonate aqueous solution and saturated brine, and dried over magnesium sulfate. The crude amine obtained by distilling off the solvent under reduced pressure was dissolved in dichloromethane (5 mL). '(Z) — 11-octadecanoic acid (68 mg, 0.239 mmol) and 1-ethyl 3- (3-dimethylamine propane) were added. Carbodiimide hydrochloride (55 mg, 0.287 mmol), and stirred at room temperature for 20 hours. The reaction solution was diluted with dichloromethane, washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The title compound (122 mg, yield 52%) was obtained by dissolving in ethyl acetate. IR vmax (CHCl3) 3 004, 2928, 2 8 5 6, 1 662 cm-1. 500 MHz! H NMR (CDC13) δ 0.88 (12H, t, J = 6.8 Hz), 1.25-1.80 (76H, m) , 1.99-2.01 (4H, m), 2.16-2.33 (4H, m), 2.85 (1H, d, J = 3.9 Hz, 〇H), 3.07 (1H, m), 3.23-3, 2 5 (2H, m), 3.29 (3H, s), 3.36 (lH, m), 3.38 (3H, s), 3.44 (lH, t, J: = 8.8 Hz), 3.4 8-3.8 4 (1 2 H, m) , 3 · 9 1 (1 H, in), 4.09 (1H, t, J 2 9.8, -120-200413400 8.8 Hz), 3.48-3.84 (1 2H, m), 3.91 (1H, m), 4.09 (1H, t, J-9-8, 8.8 Hz), 4.17 (1 H, d, J = 10.7 Hz), 4.25 (1H, q, Bu 9.8 8.8 Hz), 4.50-4.5 8 (8H, m), 4.85 (1H, d, J = 3.9 Hz), 5.19 (1H, d, J = 7.8 Hz), 5.23-5.38 (10H, m), 5.89-5.9 8 (4H? M), 6.91 (1H, d, J = 6.8 Hz, NH). MS (FAB, positive) m / z 1512 (M + K) +, 1 496 (M + Na) + · HRMS (ESI, positive), calculate 値 C80H149N〇18P2Na: 1 497.0 1 39 ; Found 値: 1 4 9 7.0 1 2 3. (5) 2-Linanoic acid ethyl 6-〇- [2-deoxy-3--0-[(r) -3-methoxydecyl] -6- 〇-methyl-2- [(Z) — 11-octadecene Amine]-4-1-monophosphonic acid-β-D-glucopyranosyl]-2 '3-21012-12-a-D-glucopyranoside (Project Db3) will (4) The obtained compound (110 mg, 0.075 mm 1) was dissolved in tetrahydrofuran (5 mL), and triphenylphosphine (9.8 mg, 0.037 mmol), triethylamine (52 pL, 0.373 mmol), and formic acid were added. (2 8 pL, 0.74 2 mm ο 1) and triphenylphosphine palladium (4.4 mg, 0.004 mmol), and stirred at 50 ° C for 5 hours. The reaction solution was concentrated under reduced pressure 'to imitate dilution, washed with 0.1 m 1 / L hydrochloric acid aqueous solution, and the chloroform layer was concentrated under reduced pressure. The obtained mixture was purified by DEA A E cellulose (acetic acid type) column chromatography, and then dissolved in a 0.05 mo 1 / L ammonium acetate solution (chloroform: methanol: water = 2: 3: 1). Dissolve in chloroform (4mL), methanol (8mL) and 0.1 mol / L hydrochloric acid aqueous solution (3.2mL), add chloroform (4mL) and 0.1mol / L hydrochloric acid aqueous solution (4mL) and wash. The chloroform layer was separated and the solvent was evaporated under reduced pressure to obtain the title compound (80 mg, yield 8 2% -121-200413400 j ° IR vmax (KBr) 3284, 3218, 3178, 3116, 2955, 2924, 2853 , 1655, 1 6 3 0 cm-1. 500 MHz] H NMR (CD 3 〇D: CDC 13 = 5: 1) δ 0.90 (12H, t, J = 6.8 Hz), 1.28-1.67 (74H, m) , 1.7 3-1.77 (2H, m), 2.01-2.03 (4H, m), 2.16 (2H, dt, J = 7.8, 18.6 Hz), 2.25 (2H, t, J = 6.8 Hz), 3.22 (1H, dd, J = 2.9, 9.8 Hz), 3.31 (3H, s), 3.34 (lH, m), 3.41 (3H, s), 3.46 (lH, t, J = 9.8, 8.8Hz), 3.54-3.85 (15H , M), 3.96 (1H, m), 4.07-4.12 (2H, m), 4.54 (1H, d, J = 8.8 Hz). 4.87 (1H, d, J = 3.9 Hz), 5.31-5.37 (2H, m). [Example 8] Phosphonic acid group 6-0- {2-deoxy-3-0-[(R) -3-methoxydecyl] -6-O-methyl-2-2- [(Z ) — 11 mono (octadecenyl) amino]-4-10-phosphonic acid-β-D-glucopyranosyl} —3—0-dodecyl—2—0 — [(R )-3 -Hydroxytetradecyl] -a-D -glucopyranoside (1) 1,2: 5,6 -di-0 — Isopropyl-3—0-dodecyl-ex-D-furanose (Project A a 1) will be 1,2: 5,6—di-0—isopropylidene-a-D-furanose ( 2 6.0 g, 0.1 mol) and dodecyl mesylate (13.2 g, 0.05 mol) were reacted according to the method of Example 1 (1) to obtain the title compound (3 1.1 g, yield 75%). 400 MHz] H NMR (CDC13) δ 0.88 (3H? t, J = 6.6 Hz), 1.26 (18H, bs), 1.32 (3H, s), 1.35 (3H, s) , 1.43 (3H, s), 1.50 (3 H, s), 1.5 2-1.5 5 (2 H, m), 3.5 1 (1 H, m), 3, 5 9 (1 H, m ), -122-200413400 3.85 (1H, d, J = 2.9 Hz), 3.98 (1H, m), 4.0 6-4 izi * 14 (3H, m) 5 4.31 (1H, m), 4.52 (1H, d , J 2 3.7 Hz), 5.88, UH, d, J: 3 7

Hz) · ϋ〜吡喃葡糖苷（第 mmol)加入含2%鹽 (2 )烯丙基3 — O —十二基一 α，β — A a 2工程）將（1 )所得化合物（900mg，2.160 酸之細丙醇（1 〇 ni L ) ’將反應液回流2 〇分。將反應液濃Hz) · ϋ ~ glucopyranoside (No. mmol) added with 2% salt (2) allyl 3-O-dodecyl-α, β-A a 2 Project) The compound (1) (900 mg, 2.160 fine propanol (10 ni L) of acid 'reflux the reaction solution for 20 minutes. The reaction solution is concentrated

縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（1 : i，再以1 : 3 )，可得油狀標題化合物α體（674mg，產率 80% )及 β 體（64mg，產率 8% )。 (X體：And then purified by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (1: i, then 1: 3) to obtain the oily compound α-form (674mg, yield 80%) and β-form (64mg, yield 8%). (Body X:

Rf = 0.23 (環己烷-EtOAc (1:1)). mp 7 2-7 3.5 T：(針狀晶）· IR vmax (KBr) 3 306, 2920, 2852 cm'1.Rf = 0.23 (cyclohexane-EtOAc (1: 1)). Mp 7 2-7 3.5 T: (acicular crystal) · IR vmax (KBr) 3 306, 2920, 2852 cm'1.

400 MHz ]H NMR (CDC13) δ 0.88 (3H, t, 1 = 6.6 Hz), 1.26 (18H, bs), 1.59- 1.64 (2H, m), 2.19 (1H, d, J = 9.5 Hz, OH), 2.24 (1H, t, J = 6.3 Hz, OH), 2.79 (1H, d, J = 2.9 Hz, OH), 3.45 (1H, d, J = 8.8 Hz), 3.50-3.61 (2H, m), 3.64-3.71 (2H, m), 3.80-3.86 (2H, m), 3.93 (1H, m), 4.04 (1H, m), 4.23 (1 H, m), 4.90 (1H, d, J = 3.7 Hz), 5.22 - 5.34 (2H, m), 5.9 2 (1H, m). C21H4Q06 分析計算値：c，64.9 2; H，10.38。實測値：C， 64.96; H， 10.17. β體： 123 - 200413400400 MHz] H NMR (CDC13) δ 0.88 (3H, t, 1 = 6.6 Hz), 1.26 (18H, bs), 1.59- 1.64 (2H, m), 2.19 (1H, d, J = 9.5 Hz, OH) , 2.24 (1H, t, J = 6.3 Hz, OH), 2.79 (1H, d, J = 2.9 Hz, OH), 3.45 (1H, d, J = 8.8 Hz), 3.50-3.61 (2H, m), 3.64-3.71 (2H, m), 3.80-3.86 (2H, m), 3.93 (1H, m), 4.04 (1H, m), 4.23 (1 H, m), 4.90 (1H, d, J = 3.7 Hz ), 5.22-5.34 (2H, m), 5.9 2 (1H, m). C21H4Q06 Analytical calculation 値: c, 64.9 2; H, 10.38. Found 値: C, 64.96; H, 10.17. Β-body: 123-200413400

Rf二0.3 1 (環己烷-EtOAc (1:1)). 400 MHz NMR (CDC13) δ 0.88 (3H，t，J = 7.0 Hz)，1.26 (18H，bs)，1.50-1.61 (2H, m)5 3.4 6 - 3.5 3 ( 1 0H, m), 5.07 (1H，d，J二5.1 Hz)，5.21-5.42 (2H，m)，5.93 (1H，m)· (3) 烯丙基3— O —十二基一4，6— O —亞異丙基—a — D -吡喃葡糖苷（第A a 3工程）將（2 )所得化合物α體（4 7 0 m g，1 · 2 1 0 m m ο 1 )，依實施例1 ( 3 )之方法處理，可得油狀標題化合物（42Omg，8 1 % )。 _ 400 MHz lR NMR (CDC13) δ 0.88 (3H? t, 1 = 6.6 Hz), 1.26 (18H，bs)，1.41 (3H，s)，1.49 (3H, s), 1.5 3 - 1.60 (2H, m), 2.31 (1H, d，J二7·3 Hz，OH)，3·46-3·85 (8H，m)，4.04 (1H， m)，4.21 (1H，m)，4.92 (1H，d，J = 3.7 Hz), 5.22-5.34 (2H， m), 5.93 ( 1 H, m). (4) 烯丙基2 — O— [(R) — 3—(第三丁二甲矽烷氧基 )十四基]—3— O —十二基一4，6 —〇一亞異丙基一α— D — 吡喃葡糖苷（第A a 4工程）， ® 將（3 )所得化合物（9 8 0 m g，2.2 8 7 m m ο 1 )，依實施例1 (4 )之方法處理，可得蠟狀之標題化合物（1 . 5 3 3 g , 6 7 % )。 IR vniax(膜）2925, 285 6, 1464 cm.1· 400 MHz ιΗ NMR (CDC13) δ 0.04 (3H, s), 0.86-0.8 9 ( 1 5 H, m，含 9H，s，at δ 0.88ppm)，1·26 (38H，bs)，1.40 (3H, s)， 1.48 (3H, s), 1.49- 1.5 5 (2H, m)? 1.70- 1.77 (2H, m)? 3.29 (1 H , m ) · 3.4 5 - 3 . 7 8 ( 9 H，m )，3 · 8 4 ( ] H，m)，4.0 4 ( 1 H，rn )， 200413400 4.17 (1H，m)，4.91 (1Η，d，J = 3.7 Hz)，5.20-5.34 (2H，m) 5.92 (1H，m). FABMS (陽離子）m/z，7 5 5 [M + H] +，77 7 [M + Na]+ (力口入 Nal)· HRFABMS，C44H86〇7 Si Na 計算値：777.6040。實測値：7 7 7.5 9 94. (5) _丙基3— O —十二基一 2 - O - [(R) - 3〜經基十四基]一 α — D —吡喃葡糖苷（第A a 5工程）將（4 )所得化合物（9 6 5 m g，1 · 2 8 7 m m ο 1 )，依實施例ι (5)之方法處理，可得蠟狀之標題化合物（3 8 6mg,產率 5 0% )。 IR vmax (KBr) 3400-3260, 2920, 2850 cm'1. 400 MHz 】H NMR (CDC13) δ 0.8 6-0.89 (6H，m)，1.26 (3 6H, bs), 1.41-1.73 (6H, m), 2.07 (1H, bs, OH), 2.60 (1H, bs, OH), 2.96 (1H, bs, OH), 3.30 (1H, m), 3.50-3.89 ( 1 0H, m), 4.04 (1H, m), 4.20 (1H, m), 5.00 (1H, m), 5.22-5.34 (2H, m), 5.95 (1H, m). FABMS (陽離子）m/z，599 [M-H] +，601 [M + H]' 623 [M + Na] + . HRFABMS，C35H6 8 07Na 計算値：623.4862。實測値： 623.4 8 6 1 . (6) (E) — 1—丙烯基 3— Ο —癸基—2—0— [(R) 一 3 —羥基十四基]—α — D —吡喃葡糖苷（第A a 6工程）將（5 )所得化合物（38 1 mg, 0.6 3 4 mmol )，依實施例1 (6 )之方法反應，可得粉狀標題化合物（3 8 1 m g ,產率 -125 - 200413400 10 0%)。 IR vmax (KBr) 3411 (br)5 2920，2850，1 679 (w)，1 468 cm-1. 400 MHz ]H NMR (CDC13) δ 0.88 (6H，t, J = 6.6 Hz)，1.26 (36H，bs)，1.41-1.73 (9H，m)，1.86 (1H，bs，〇H)，2.45 (1H， bs，〇H)，2.72 (1H，bs，〇H)，3.32 (1H，dd，J = 3.7，9.5 Hz)， 3.49-3.92 ( 1 0H, m), 5.16-5.23 (2H? m), 6.19 (1H, m). FABMS (陽離子）m/z，601 [M + H] +，623 [M + Na] + . H R F A B M S C 3 5 H 6 8 〇 7 N a 計算値：6 2 3 _ 4 8 6 2。實測値： 623.48 80. (7) (E) — 1—丙烯基6 —〇一（第三丁二甲矽烷基）一 3 - 0 —十二基—2 - 0— [(R) — 3 —羥基十四基]—α— D 一吡喃葡糖苷（第A a 7工程）將（6 )所得化合物（747 mg, 1 · 24 3 mmol )，依實施例1 (7)之方法反應，可得粉狀標題化合物（670 mg，產率 75% )。 IR vmax (KBr) 3226, 2925, 2853, 1749, 1467 cm1. 400 MHz 'H NMR (CDC13) δ 0.08 (6H, s)? 0.88 (3H, t, J = 6.6 Hz), 0.90 (9H, s), 1.26 (36H, bs), 1.40-1.73 (7H, m, 含 3H，dd，J=1.5，6.6 Hz，at δ 1.55 ppm), 2.74 (1H，bs, 〇H)，2·81 (1H，bs，OH)，3.30 (1H, m)，3.51-3.87 (10H，m)， 5. 14 (1H，d，J = 3.7 Hz). FABMS (陽離子）m/z，715 [M + H] +，737 [M + Na] + . H R F A B M S C 4 ! H 8 2 〇 7 S i N a 言十算値：7 3 7.5 7 2 8。實測値： 7 3 7 . 5 7 3 0 . -126 - 200413400 (8 } ( E ) — 1 —丙豨基4 —〇一烯丙氧羰基一2 —〇一[ (R ) — 3 — （烯丙氧羰氧基）十四基]一 6 一〇一（第三丁二甲矽烷基）一 3 — 〇一十二基一 α 一 D 一吡喃葡糖苷（第a a 8工程）料（7 )所侍化g物（6 $ 9 m g , 〇 . 9 2 1 in m ο 1 )，依實施例1 (8 )之方法反應’可得標題化合物（813mg，產率100% ) IR vmax(fe) 2927, 2856, 1 749, 1 680, 1 464, 1 37 1 cm"1. 4〇0 MHz lU NMR (CDC13) δ 〇.〇2 (3H, s), 0.03 (3H, s), φ 0.86-0.90 (15H，m，含 9H, s，at δ 0.88 ppm), 1.25 (36H，bs), 1.46-1.63 (7H，m，含 3H，dd，J = 2.2，6.6 Hz, at δ 1.54 ppm)， !.88-1.91 (2H, m), 3.35 (1H, m), 3.53 (1H, m), 3.65-3.80 (7H, m), 4.59-4.65 (4H, m), 4.71 (1H, t, J = 9.9 Hz), 4.78 (1H, m), 5.09 (1H, d, J = 3.7 Hz), 5.18 (1H, m), 5.25-5.39 (4H, m), 5.89-5.98 (2H, m), 6.17 (1H, qd, J-2.2, 12.5 Hz). (9) 4 一〇一烯丙氧羰基一 2 — O— [(R) — 3—(烯丙氧羰氧基）十四基]一 3— O —十二基—D—吡喃葡糖（第Aa _ 9工程）將（8 )所得化合物（8 4 0 m g，0 · 9 5 1 m m ο 1 )，依實施例1 (9 )之方法反應，可得標題化合物（64〇mg，產率64% ) IR vmax(膜）3 527 (br)，2925，2 854，1 747，1 679 (w) cm-1· 400 MHz !H NMR (CDC13) δ 0.88 (6H，t, J二6.6 Hz)，1.25 (36H，bs)，1.50-1.65 (7H，m，含 3H，dd, J =1.5, 6.6 Hz，at δ -127 - 200413400 1.55 ppm), 1.87-1.92 (2H, m)，2·33 (1H，bs，〇 Η)，3.37 (1H， dd，J = 2.9，9.5 Hz), 3.55-3.81 (8H，m)，4.60-4.67 (4H，m)5 4.72 (1H，m)，4.80 (1H，m)，5.13 (1H, d，J二3.7 Hz)，5.18 (1H，qd，J = 6.6，12.5 Hz), 5.25-5.40 (4H，m)，5.89-5.98 (2H, m)，6.16 (1H，qd, J 二 1.5, 12.5 Hz). FABMS (陽離子）m/z，768 [M + H] +，791 [M + Na] + · HRFABMS C43H7 !Na 計算値：7 9 1.5 2 8 6。實測値： 79 1.528 1. (10) (E) -1 一丙儲基 2— O-〔（R) — 3—(燦丙氧鑛氧基）十四基〕一 6— Ο - {2 -去氧一 4一 Ο—二烯丙鱗酸基一 3 — 0 —〔（R) — 3 —甲氧癸基〕一 6 — 0 一甲基一 2 一〔（2，2，2—三氯乙氧羰基）胺基〕一 β— D—毗喃葡糖基}一3— 0—十二基一 a— D-吡喃葡糖苷（第C a 1工程）將（9 )所得化合物（6 0 6 m g，0.7 1 8 m m ο 1 )，依實施例1 (10 )之方法反應，可得標題化合物（867mg,產率100% )0 IR vmax(膜）3 400-3 080 (w)，2927, 285 6，1 7 45 cm'1. 400 MHz ]H NMR (CDC13) δ 0.88 (9H, t, J = 6.6 Hz), 1.25-1.30 (48H，m)，1.38-1.75 (9H，m)，1.85-1.90 (2H，m)，3.23-3.80 (22H, m，含 2 個 3H，s，at δ 3.28 and 3.3 8 ppm), 4.0 4 (1 H, d，J= 1 1.7 Hz), 4.26 (1H，dd, J = 9.5，18.3 Hz), 4.51-4.85 (12H, m), 5.10 ( 1 H, d, J = 3.7 Hz), 5.16 (1H, m), 5.23-5.40 (8H, m), 5 . 8 9 - 5 . 9 9 ( 1 H，m)，6.6 2 (4 H，m ), 6 . 1 6 ( 1 H , d d，J 二 1 . 5，12.5 Hz). -128 - 200413400 FABMS (陽離子）m/z, 1 470 [M + Na，35C1] +，1 472. H R F A B M S C 7 〇 H ! 2! C 13 N 〇 2 ] P N a 計算値：1 4 7 0 · 7 1 3 2。實測値：1470.7102. (11) (E) — 1 一丙;希基4一 O —稀丙氧羰基一 2 — 0—〔 (R) — 3-（烯丙氧羰氧基）十四基〕—3 - ◦一十二基一 6 一 Ο — { 2 一去氧一4—0 — _儲丙鱗酸基一3—0—〔（R) —3—甲氧癸基〕一6— Ο—甲基一2— 〔（Ζ) — 11—(十八碳烯醯基）胺基〕一 β - D —吡喃葡糖基丨一 α - D -毗喃葡糖苷（第Ca2工程）籲將（1 0 )所得化合物（8 9 5 m g，0.6 1 7 m m ο 1 )，依實施例1 (11)之方法反應，可得油狀標題化合物（428mg,產率 4 5%)。 IR vmax(膜）3 3 06 (w), 2926, 28 5 5, 1 747, 1 67 8, 1 65 9，1 547， 1465 cm"1. 400 MHz lR NMR (CDC13) δ 0.88 (12H, t, J-6.6 Hz), 1.25 (66H，bs) 1.40- 1.80 ( 1 3H，m，含 3H，dd，J=1.5，6.6 Hz，at δ 1.54 ppm), 1.84- 1.89 (2H, m) 2.00-2.05 (4H, m), 2.22-2.26 鲁 (2H，m)，3.22-3.79 (20H，m,含 2 個 3H，s，at δ 3.28 and 3.37 ppm), 3.85 (1H, m), 4.04 (1H, m), 4.24 (1H, m), 4.53-4.72 (10H，m)，4.7 8 -4.84 (2H，m)，5.09 (1H，d，J = 3.7 Hz)， 5.16 (1H，m)，5.22-5.41 (10H，m)，5.88-5.99 (4H，m), 6.05 (1H, d，J = 8.1 Hz), 6·13 (1H，dd，J二 1.5，12.5 Hz). FABMS (陽離子）m/z，1 5 6 0 [M. + Na] + . H R F A B M S C 8 5 H i 5 2 N 〇 2 ο P N a 言十算値：1 5 6 1.0543。實測値： -129 - 200413400 1561.0560. (12) 4— Ο —烯丙氧羰基一2—0-〔（R) — 3-（烯丙氧羰氧基）十四基〕一 3— Ο—十二基一 6— Ο - {2-去氧—4 一 Ο —二烯丙膦酸基一 3— Ο—〔（R) — 3 —甲氧癸基〕一 6 — Ο —甲基一 2 — [ ( Z ) 一 11 一（十八石灰細酿基）月女基〕一0—〇—舭喃葡糖基}—€6—〇—卩比喃匍糖（弟〇3 3工程）將（i i )所得化合物（421mg，0.274mmol )，依實施例1 (1 2 )之方法反應，可得蠟狀之標題化合物（2 7 4 m g ,產 _ 率 6 7 % )。 IR vmax(膜）3300 (w)，2926，2855，1 748，1 652，1 549，1465 cm'1. 400 MHz lH NMR (CDC13) δ 0.86-0.88 (12H, m), 1.25 (66H, bs)，1.40- 1.90 ( 1 3H，m，含〇《〇,1.92-2.04 (41*1，111)，2.16-2· 19 (2H，m)，3.08- 3.77 (20H，m，含 3 H，s，at 3.27 ppm, and 3 H, s, at 3.38 ppm)，3.85-4.63 (14H，m)，4.82 (1H，m)， 5.23 -5.40 ( 1 1 H，m)，5.8 8 -5.98 (4H，m)，6.05 (1H，d, J = 7.3 _Rf di 0.3 1 (cyclohexane-EtOAc (1: 1)). 400 MHz NMR (CDC13) δ 0.88 (3H, t, J = 7.0 Hz), 1.26 (18H, bs), 1.50-1.61 (2H, m ) 5 3.4 6-3.5 3 (1 0H, m), 5.07 (1H, d, J 5.1 Hz), 5.21-5.42 (2H, m), 5.93 (1H, m) · (3) allyl 3— O —dodecyl-4,6 — O —isopropylidene —a — D -glucopyranoside (Project A a 3) The compound (2) obtained as the alpha form (4 7 0 mg, 1 · 2 1 0 mm ο 1), treated according to the method of Example 1 (3), to obtain the title compound (42Omg, 81%) as an oil. _ 400 MHz lR NMR (CDC13) δ 0.88 (3H? T, 1 = 6.6 Hz), 1.26 (18H, bs), 1.41 (3H, s), 1.49 (3H, s), 1.5 3-1.60 (2H, m ), 2.31 (1H, d, J = 7.3 Hz, OH), 3.46-3 · 85 (8H, m), 4.04 (1H, m), 4.21 (1H, m), 4.92 (1H, d , J = 3.7 Hz), 5.22-5.34 (2H, m), 5.93 (1 H, m). (4) Allyl 2 — O— [(R) — 3— (tertiary butanesilyloxy ) Tetradecyl] —3—O—dodecyl-4,6—0—isopropylidene—α—D—glucopyranoside (Project Aa 4), (3) The obtained compound (9 80 mg, 2.2 8 7 mm ο 1), treated according to the method of Example 1 (4), to obtain the title compound (1.53 g, 67%) as a wax. IR vniax (film) 2925, 285 6, 1464 cm. 1.400 MHz ιΗ NMR (CDC13) δ 0.04 (3H, s), 0.86-0.8 9 (1 5 H, m, including 9H, s, at δ 0.88ppm ), 1.26 (38H, bs), 1.40 (3H, s), 1.48 (3H, s), 1.49- 1.5 5 (2H, m)? 1.70- 1.77 (2H, m)? 3.29 (1 H, m ) · 3.4 5-3. 7 8 (9 H, m), 3 · 8 4 (] H, m), 4.0 4 (1 H, rn), 200413400 4.17 (1H, m), 4.91 (1Η, d, J = 3.7 Hz), 5.20-5.34 (2H, m) 5.92 (1H, m). FABMS (cation) m / z, 7 5 5 [M + H] +, 77 7 [M + Na] + (force port Enter Nal) HRFABMS, C44H86〇7 Si Na Calculated 値: 777.6040. Found 値: 7 7 7.5 9 94. (5) _propyl 3 — O —dodecyl 2 — O — [(R)-3 to tetradecyl]] — α — D —glucopyranoside ( Process A a 5) The compound obtained in (4) (965 mg, 2.7 8 mm ο 1) was treated in accordance with the method of Example ι (5) to obtain the title compound (3 8 6 mg) , Yield 50%). IR vmax (KBr) 3400-3260, 2920, 2850 cm'1. 400 MHz] H NMR (CDC13) δ 0.8 6-0.89 (6H, m), 1.26 (3 6H, bs), 1.41-1.73 (6H, m ), 2.07 (1H, bs, OH), 2.60 (1H, bs, OH), 2.96 (1H, bs, OH), 3.30 (1H, m), 3.50-3.89 (1 0H, m), 4.04 (1H, m), 4.20 (1H, m), 5.00 (1H, m), 5.22-5.34 (2H, m), 5.95 (1H, m). FABMS (cation) m / z, 599 [MH] +, 601 [M + H] '623 [M + Na] +. HRFABMS, C35H6 8 07Na Calculated 値: 623.4862. Measured fluorene: 623.4 8 6 1. (6) (E) — 1-propenyl 3 — 0 —decyl — 2-0 — [(R) —3 —hydroxytetradecyl] —α — D —glucopyranose Glycoside (Project A a 6) The compound (38 1 mg, 0.6 3 4 mmol) obtained in (5) was reacted according to the method of Example 1 (6) to obtain the title compound (3 8 1 mg, yield). -125-200413400 10 0%). IR vmax (KBr) 3411 (br) 5 2920, 2850, 1 679 (w), 1 468 cm-1. 400 MHz] H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (36H , Bs), 1.41-1.73 (9H, m), 1.86 (1H, bs, 0H), 2.45 (1H, bs, 0H), 2.72 (1H, bs, 0H), 3.32 (1H, dd, J = 3.7, 9.5 Hz), 3.49-3.92 (1 0H, m), 5.16-5.23 (2H? M), 6.19 (1H, m). FABMS (cation) m / z, 601 [M + H] +, 623 [M + Na] +. HRFABMSC 3 5 H 6 8 〇7 N a Calculated 値: 6 2 3 _ 4 8 6 2. Measured rhenium: 623.48 80. (7) (E) — 1-propenyl 6 — 〇— (third butyl dimethylsilyl) — 3-0 —dodecyl — 2-0— [(R) — 3 — Hydroxytetradecyl] -α-D-glucopyranoside (Project A a 7) The compound (747 mg, 1.24 3 mmol) obtained in (6) can be reacted according to the method of Example 1 (7). The title compound was obtained as a powder (670 mg, 75% yield). IR vmax (KBr) 3226, 2925, 2853, 1749, 1467 cm1. 400 MHz 'H NMR (CDC13) δ 0.08 (6H, s)? 0.88 (3H, t, J = 6.6 Hz), 0.90 (9H, s) , 1.26 (36H, bs), 1.40-1.73 (7H, m, including 3H, dd, J = 1.5, 6.6 Hz, at δ 1.55 ppm), 2.74 (1H, bs, 0H), 2.81 (1H, bs, OH), 3.30 (1H, m), 3.51-3.87 (10H, m), 5. 14 (1H, d, J = 3.7 Hz). FABMS (cation) m / z, 715 [M + H] + , 737 [M + Na] +. HRFABMSC 4! H 8 2 〇7 Si N a Count: 7 3 7.5 7 2 8. Measured fluorene: 7 3 7. 5 7 3 0. -126-200413400 (8} (E) — 1 -propanyl 4 —〇-allyloxycarbonyl — 2 —〇— [(R) — 3 — (ene Propoxycarbonyloxy) tetradecyl] -1 6 10 (Third-Butylsilyl)-3-0-12 Dodecyl-α-D-glucopyranoside (Project aa 8) Project (7 ) G of the compound (6 $ 9 mg, 0.92 1 in m ο 1), the reaction according to the method of Example 1 (8) to obtain the title compound (813mg, yield 100%) IR vmax (fe ) 2927, 2856, 1 749, 1 680, 1 464, 1 37 1 cm " 1.400 MHz lU NMR (CDC13) δ 0.02 (3H, s), 0.03 (3H, s), φ 0.86 -0.90 (15H, m, including 9H, s, at δ 0.88 ppm), 1.25 (36H, bs), 1.46-1.63 (7H, m, including 3H, dd, J = 2.2, 6.6 Hz, at δ 1.54 ppm) , ..88-1.91 (2H, m), 3.35 (1H, m), 3.53 (1H, m), 3.65-3.80 (7H, m), 4.59-4.65 (4H, m), 4.71 (1H, t, J = 9.9 Hz), 4.78 (1H, m), 5.09 (1H, d, J = 3.7 Hz), 5.18 (1H, m), 5.25-5.39 (4H, m), 5.89-5.98 (2H, m), 6.17 (1H, qd, J-2.2, 12.5 Hz). (9) 4 10-allyloxycarbonyl-2 — O— [(R) — 3— (allyl Carbonyloxy) tetradecyl]-3—O—dodecyl—D—glucopyranose (Section Aa_9) will be obtained from (8) (8 4 0 mg, 0 · 9 5 1 mm ο 1 ), According to the method of Example 1 (9), the title compound (64 mg, yield 64%) IR vmax (membrane) 3 527 (br), 2925, 2 854, 1 747, 1 679 (w ) cm-1 · 400 MHz! H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.25 (36H, bs), 1.50-1.65 (7H, m, including 3H, dd, J = 1.5, 6.6 Hz, at δ -127-200413400 1.55 ppm), 1.87-1.92 (2H, m), 2.33 (1H, bs, 0Η), 3.37 (1H, dd, J = 2.9, 9.5 Hz), 3.55- 3.81 (8H, m), 4.60-4.67 (4H, m) 5 4.72 (1H, m), 4.80 (1H, m), 5.13 (1H, d, J = 3.7 Hz), 5.18 (1H, qd, J = 6.6, 12.5 Hz), 5.25-5.40 (4H, m), 5.89-5.98 (2H, m), 6.16 (1H, qd, J 2 1.5, 12.5 Hz). FABMS (cation) m / z, 768 [M + H] +, 791 [M + Na] + · HRFABMS C43H7! Na Calculated 値: 7 9 1.5 2 8 6 Measured erbium: 79 1.528 1. (10) (E) -1 1-Propyl 2—O-[(R) — 3— (Canpropoxyloxy) tetradecyl] —6— Ο-{2- Deoxy-4,10-diallylic phosphono- 3-0-[(R)-3 -methoxydecyl]-6-0 -methyl-2 2-[(2,2,2-trichloro Ethoxycarbonyl) amino] -β-D-pyranoglucosyl} -3-0-dodecyl-a-D-glucopyranoside (Project C a 1) The compound (9) obtained (6 0 6 mg, 0.7 1 8 mm ο 1), reacted according to the method of Example 1 (10) to obtain the title compound (867 mg, yield 100%) 0 IR vmax (membrane) 3 400-3 080 (w), 2927, 285 6, 1 7 45 cm'1. 400 MHz] H NMR (CDC13) δ 0.88 (9H, t, J = 6.6 Hz), 1.25-1.30 (48H, m), 1.38-1.75 (9H, m) , 1.85-1.90 (2H, m), 3.23-3.80 (22H, m, including two 3H, s, at δ 3.28 and 3.3 8 ppm), 4.0 4 (1 H, d, J = 1 1.7 Hz), 4.26 (1H, dd, J = 9.5, 18.3 Hz), 4.51-4.85 (12H, m), 5.10 (1 H, d, J = 3.7 Hz), 5.16 (1H, m), 5.23-5.40 (8H, m) , 5.8 9-5.9 9 (1 H, m), 6.6 2 (4 H, m), 6. 1 6 (1 H, dd, J 2 1 5, 12.5 Hz). -128-200413400 FABMS (cation) m / z, 1 470 [M + Na, 35C1] +, 1 472. HRFABMSC 7 〇H! 2! C 13 N 〇2] PN a Calculate 値: 1 4 7 0 · 7 1 3 2. Measured 0.7: 1470.7102. (11) (E) — 1 monopropyl; cis 4 — O — dilute propoxycarbonyl — 2 — 0 — [(R) — 3- (allyloxycarbonyloxy) tetradecyl] —3-◦Dodecyl-6—O— — 2 2-Deoxy-4—0 — _Propanyl—3—0 — [(R) —3-methoxydecyl] —6—O —Methyl-2 — [(Z) —11— (octadecenyl) amino] -β-D-glucopyranosyl 丨 α-D-pyranoglucoside (Project Ca2) The compound (8 9 5 mg, 0.6 1 7 mm ο 1) obtained in (10) was reacted according to the method of Example 1 (11) to obtain the title compound (428 mg, yield 45%) as an oil. IR vmax (film) 3 3 06 (w), 2926, 28 5 5, 1 747, 1 67 8, 1 65 9, 1 547, 1465 cm " 1. 400 MHz lR NMR (CDC13) δ 0.88 (12H, t , J-6.6 Hz), 1.25 (66H, bs) 1.40- 1.80 (1 3H, m, including 3H, dd, J = 1.5, 6.6 Hz, at δ 1.54 ppm), 1.84- 1.89 (2H, m) 2.00- 2.05 (4H, m), 2.22-2.26 Lu (2H, m), 3.22-3.79 (20H, m, including 2 3H, s, at δ 3.28 and 3.37 ppm), 3.85 (1H, m), 4.04 (1H , m), 4.24 (1H, m), 4.53-4.72 (10H, m), 4.7 8 -4.84 (2H, m), 5.09 (1H, d, J = 3.7 Hz), 5.16 (1H, m), 5.22 -5.41 (10H, m), 5.88-5.99 (4H, m), 6.05 (1H, d, J = 8.1 Hz), 6 · 13 (1H, dd, J = 1.5, 12.5 Hz). FABMS (cation) m / z, 1 5 6 0 [M. + Na] +. HRFABMSC 8 5 H i 5 2 N 〇 PN a Count: 1 5 6 1.0543. Measured plutonium: -129-200413400 1561.0560. (12) 4—O—allyloxycarbonyl—2—0-[(R) —3- (allyloxycarbonyloxy) tetradecyl] —3—0—ten Diyl-6-O- {2-deoxy-4-10-diallylphosphonic acid- 3-0-[(R) -3-methoxydecyl] -6-O-methyl-2 [(Z) 1-1 (18 lime fine brewing base) moon female base]-0-0-glucopyranosyl}-€ 6-0-glucopyranose (brother 03 project) will ( ii) The obtained compound (421 mg, 0.274 mmol) was reacted according to the method of Example 1 (12) to obtain the title compound (27.4 mg, yield 67%) as a wax. IR vmax (film) 3300 (w), 2926, 2855, 1 748, 1 652, 1 549, 1465 cm'1. 400 MHz lH NMR (CDC13) δ 0.86-0.88 (12H, m), 1.25 (66H, bs ), 1.40-1.90 (1 3H, m, containing 0, 0, 1.92-2.04 (41 * 1, 111), 2.16-2 · 19 (2H, m), 3.08- 3.77 (20H, m, containing 3 H, s, at 3.27 ppm, and 3 H, s, at 3.38 ppm), 3.85-4.63 (14H, m), 4.82 (1H, m), 5.23 -5.40 (1 1 H, m), 5.8 8 -5.98 (4H , M), 6.05 (1H, d, J = 7.3 _

Hz, NH). FABMS (陽離子）m/z，1 5 20 [M + Na] + . HRFABMS, C82Hi48N〇20PNa 計算値：1 5 2 1.0 2 3 0。實測値： 1521.0250. (13) 二烯丙膦酸基4一〇一烯丙氧羰基一 2 —〇一〔（ R) — 3—（嫌丙氧羰氧基）十四基〕一 3 - 0—十二基一 6 —〇--{ 2 —去氧一4 一〇 —二烯丙膦酸基一 3 — Ο —〔（ R ) — -130 - 200413400 3—甲氧癸基〕一6 — 0 —甲基一 2— 〔（z) — 11 — （十八碳烯醯基）胺基〕—β - D -吡喃葡糖基丨一 α 一 d -吡喃葡糠苷（α體）及二烯丙膦酸基 4 一〇 -烯丙氧羰基一 2 - 0 一〔（R) — 3—（烯丙氧羰氧基）十四基〕一 3— Ο—十二基一 ό —〇一丨2—去氧一4— Ο—二稀丙膦酸基一 3 —〇一〔（ R) — 3 —甲氧癸基〕一6 —〇一甲基—2— 〔（Ζ) — 11 — (十八碳烯醯基）胺基〕一 β - 比喃葡糖基}-β - D-吡喃葡糖苷（β體）（第C a 4工程）將（12 )所得化合物（265mg，〇.i77mmol )，依實施例 1 (13)之方法反應，可得標題化合物α體（I38mg，產率 4 7 % )及β體（1 4 1 mg，產率4 8 % )油狀化合物。 α體： IR vmax(膜）3 3 06 (w)，2926, 285 6，1 747，1 660，1 548 cm-1· 400 MHz ^ NMR (CDC13) δ 0.86-0.90 ( 1 2Η, m), 1.25 (66H, bs), 1.40-2.05 ( 1 6H, m), 2.21-2.25 (2H, m), 3.22-4.06 (23H, m，含 2 個 3H, s, at 3.28 and 3.38 ppm), 4.26 (1H, dd, 9.5, 18.3 Hz), 4.54-4.62 ( 1 2H, m), 4.64-4.73 (2H, m), 4.78 (1H，t，J = 5.9 Hz)，5.23-5.43 (14H，ni)，5.72 (1H，dd，J = 3.7, 6.6 Hz)，5.88-6.01 (6H，m)，6·54 (1H，d，J = 8.1 Hz，NH)· FABMS (陽離子）m/z，1 68 0 [M + Na] + . β體： IR vmax(膜）3 309 (w)，2926，28 5 6, 1 748, 1 67 8，1 5 50，1462 c m" 1 . 400 MHz NMR (CDC13) δ 0.8 6-0.90 ( 1 2H，m)，1.2 6 ( 6 6 H， 200413400 bs)，1.40-2.07 (16H, m)，2.21-2.24 (2H，m)，3.18-3.86 (22H，m，含 2 個 3H，s，at 3.27 and 3·38 ppm)，3.99 (1H，m); 4.25 (1H，dd，9.5, 18.3 Hz), 4.43 -4.65 (12H，m)，4.70 (1H， d，J二 8.8 Hz)，4.78 (1H，m)，4.93 (1H，dd, J = 5.1，8.1 Hz)， 5.19-5.43 (14H，m)，5.86-6.00 (6H，m)，7.48 (1H，d, J 二 9.5Hz, NH). FABMS (cation) m / z, 1 5 20 [M + Na] +. HRFABMS, C82Hi48N020PNa Calculated 値: 1 5 2 1.0 2 3 0. Measured fluorene: 1521.0250. (13) diallylphosphonic acid group 4-10 allyloxycarbonyl group 2-0 — [(R) — 3— (probyloxycarbonyloxy) tetradecyl]] 3-0 —Dodecyl-6—〇-{2 —Deoxy-4 10—Diallylphosphonic acid group 3 — 0 — [(R) — -130-200413400 3—methoxydecyl] 6— 0—methyl-1 — [(z) — 11— (octadecenyl) amino] -β-D-glucopyranosyl-α-d-glucopyranoside (alpha form) And diallylphosphonic acid group 4 10-allyloxycarbonyl group 2-0-[(R) — 3-(allyloxycarbonyloxy) tetradecyl]-3-0-dodecyl 1th — 〇一丨 2—Deoxy-4—0—dipropanephosphonic acid group—3—〇 — [(R) —3-methoxydecyl] —6-—O-methyl-2— [(Z) — 11 — (octadecenylamino) amino] -β-pyranoglucosyl} -β-D-glucopyranoside (β-body) (Project C a 4) The compound obtained in (12) (265mg , I. 77 mmol), according to the method of Example 1 (13), the title compound α body (I38 mg, yield 47%) and β (1 4 1 mg, yield 48%) as an oil compound. Alpha body: IR vmax (film) 3 3 06 (w), 2926, 285 6, 1 747, 1 660, 1 548 cm-1 · 400 MHz ^ NMR (CDC13) δ 0.86-0.90 (1 2Η, m), 1.25 (66H, bs), 1.40-2.05 (16H, m), 2.21-2.25 (2H, m), 3.22-4.06 (23H, m, including 2 3H, s, at 3.28 and 3.38 ppm), 4.26 ( 1H, dd, 9.5, 18.3 Hz), 4.54-4.62 (1 2H, m), 4.64-4.73 (2H, m), 4.78 (1H, t, J = 5.9 Hz), 5.23-5.43 (14H, ni), 5.72 (1H, dd, J = 3.7, 6.6 Hz), 5.88-6.01 (6H, m), 6.54 (1H, d, J = 8.1 Hz, NH), FABMS (cation) m / z, 1 68 0 [M + Na] +. Β-body: IR vmax (membrane) 3 309 (w), 2926, 28 5 6, 1 748, 1 67 8, 1 5 50, 1462 c m " 1. 400 MHz NMR (CDC13) δ 0.8 6-0.90 (1 2H, m), 1.2 6 (6 6 H, 200413400 bs), 1.40-2.07 (16H, m), 2.21-2.24 (2H, m), 3.18-3.86 (22H, m, inclusive 2 3H, s, at 3.27 and 3.38 ppm), 3.99 (1H, m); 4.25 (1H, dd, 9.5, 18.3 Hz), 4.43 -4.65 (12H, m), 4.70 (1H, d, J Two 8.8 Hz), 4.78 (1H, m), 4.93 (1H, dd, J = 5.1, 8.1 Hz), 5.19-5.43 (14H, m), 5.86-6.00 (6H, m), 7.48 (1H, d, J Tuesday 9 .5

Hz, NH). FABMS (陽離子）m/z，1 6 80 [M + Na] + . HRFABMS，C88H157N023 P2Na 計算値：1 6 8 1.05。實測値： 1681.05. (14) 膦酸基 6— Ο— {2 —去氧一3— Ο— 〔（R) — 3 — 甲氧癸基〕一 6 — O—甲基一2—〔（Z) — 11一（十八碳烯醯基）胺基〕一 4一 Ο-膦酸基一 β— D —吡喃葡糖基}一 3-〇一十二基一2 —〇一[(R) — 3 —羥基十四基]—α—D —吡喃葡糖苷（第C a5工程）將（13 )所得化合物α體（140mg，0.084mmol )，依實施例1 ( 14)之方法反應，可得粉狀標題化合物（45 mg，產率4 0 % )。 IR vmax (KBr) 3 2 8 9 (w), 3077 (w), 2924, 285 3, 1 627, 1 5 56， 1467 cm'1 . 400 MHz NMR (CDCI3-CD3OD, 5:1) δ 0.86-0.90 (12H, m), 1.27 (66H, bs)5 1.40-1.74 (12H, m), 1.97-2.02 (4H, m), 2.2 2 - 2.2 4 ( 2 H，m)，3 · 2 2 - 4 . 1 3 ( 2 6 H，m，含 2 個 3 H，s a t 3 . 3 0 and 3.40 ppm), 4.77 ( 1 H，d，J = 7.3 H z )，5 . 3 5 - 5 · 3 9 ( 2 H , m )， 5.7 2 ( 1 H , m). -132 - 200413400 FABMS (陰離子）m/z，1328 [Μ - H]-，1 3 5 0 [M + Na-2Hr. HRFABMS，C68H132N〇19P2 計算値：1 3 2 8.8 8 7 1。實測値： 1 3 2 8.8 8 7 3 . 〔實施例9〕鱗酸基6 — 0 — {2 —去氧一 3 — Ο —〔（R) — 3 一甲氧癸基〕一6—0—甲基一2—〔（Z) — 11 一（十八碳嫌釀基）胺基〕一 4一〇一膦酸基一 β - D-吡喃葡糖基丨—3 — Ο-十二基一 2 - Ο— [(R) —3 —羥基十四基]—β - D—吡喃葡糖苷 (第C a 5工程） _ 將實施例8 ( 13 )所得化合物β體（150mg，0.090mmol ) ’依實施例1 ( 1 4 )之方法反應，可得粉狀標題化合物（ 45mg，產率 37%)。 400 MHz ln NMR (CDCI3-CD3OD, 5:1) δ 0.88 (12Η, t, J = 6.6 Hz), 1.26 (66H，bs)，1.41-1.74 (12H, m), 2.00-2.04 (4H, m), 2.24-2.28 (2H，m)，3·12-4·07 (26H，m，含 2 個 3H, s at 3.30 and 3.40 ppm), 4.92-4.97 (2H? m), 5.34-5.3 6 (2H, m). 鲁 FABMS (陰離子）m/z, 1 328 [Μ-ΗΓ. C68H133N〇19P2 分析計算値：c，61.38; H，10.07; N，1.05; P， 4·66 ° 實測値：C，61.00; H，9·97; N，1.12; P，4.24. 〔實施例1 〇〕膦酸基{2 —去氧—3— O—〔（R) -甲氧癸基〕—6 一0 一甲基一 2 —〔（ Z ) — 1 1 一（十八碳烯醯基）胺基〕一 4〜0 —膦酸基一 β - D —毗喃葡糖基丨一 2，3 -二一 Ο -133 - 200413400 一十二基一 α - D —毗喃葡糖苷 (1) 烯丙基2，3—二一〇一十二基一 4，6—0 —亞異丙基一 cx - D —吡喃葡糖苷（第A a 4工程）將貫施例8 ( 3 )所得燒丙基3 — Ο —十二基一 4，6 —〇— 亞異丙基—α — D —吡喃葡糖苷（2.90g，1 1 · 14mmol )，使用烷化劑及溴十二烷，依實施例1 ( 4 )之方法反應，可得蠟狀之標題化合物（6.4 9 g ,產率9 8 % )。 400 MHz NMR (CDC13) δ 0.88 (3H, t, J-6.6 Hz), 1.26 (36H, bs), 1.41 (3H, s), 1.48 (3H, s), 1.50- 1.60 (4H, m), 3.30 ( 1H, m), 3.49-3.74 (8H, m), 3.83 (1H, m)? 4.08 (1H, dd, J = 6.6, 13.3 Hz), 4.18 ( 1H, dd, J = 5. 1 , 13.3 Hz), 4.90 (1H, d, J = 3.7 Hz), 5.22 (1H, m), 5.32 (1H, m), 5.92 (1H, m) · (2) 烯丙基2，3—二一 O-十二基一 a— D—吡喃葡糖苷 (第A a 5工程）將（1 )所得化合物（6.4 0 g，1 0.7 2 2 m m ο 1 )，依實施例1 (5 )之方法反應，可得蠟狀之標題化合物（2.6 2g,產率 4 4%)。 IR vmax (KBr) 3 3 64 (br), 29 1 9, 2 850, 1 467 cm-1. 400 MHz 4 NMR (CDC13) δ 0·88 (6H，t，J = 6.6 Hz), 1·26 (36H，bs)，1.54-1.60 (4H，m)，1.95 (1H, t，J = 5.7 Hz，〇H)， 2.46 (1H，d，J = 2.9 Hz，〇H)，3.28 (1H5 m)，3.46-3.90 (8H， m), 3.9 3 (1H, m), 4.0 7 (1H, dd, J-6.6, 13.2 Hz), 4.20 (1H, d d，J = 5 . ]，1 3.2 H z )，4.9 6 ( 1 H，d，J : 3 . 7 H z ) 5 · 2 1 - 5.3 5 ( 2 H， 200413400 m), 5.93 (1H, m). FABMS (陽離子）m/z，5 5 5 [M-H]' 579 [M + Na] + . HRFABMS，C33H64〇6Na 計算値：579.4600。實測値： 57 9.4 5 8 1 . (3) (E) — 1—丙燃基 2，3 — —^―〇一十二基一a— D — 毗喃葡糖苷（第A a 6工程）將（2 )所得化合物（2.6 0 g，4.6 7 m m ο 1 )，依實施例1 ( 6)之方法反應，可得標題化合物（2.60g，產率100%)。 IR vmax (KBr) 3 34 1 (br), 2919, 2851, 1678 (w), 1468 cm-1. 400 MHz 4 NMR (CDC13) δ 0·88 (6H，t，J = 6.6 Hz)，1·26 (36H，bs)，1.55- 1.60 (9H, m)，1.89 (1H，bs，〇H)，2.50 (1H， m，〇H)，3.30 (1H，dd, J = 3.7, 8.8 Hz)，3·46-3·78 (6H，m)， 3.7 0- 3.84 (2H，m)，3·93 (1H，m), 5.12 (1H，d，J二 3.7 Hz)， 5.19 (1H，qd，J = 6.6，12.5 Hz), 6.18 (1H, dd, J 二 1.5，12.5 Hz). FABMS (陽離子）m/z, 5 5 5 [M-H] +，579 [M + Na] + · (4) (E)— 1 —丙烯基6—〇一（第三丁二甲矽烷基）一 2，3 — 一 — 0 —十一基一 a— D-卩比喃葡糖甘（第A a 7工程）將（3 )所得化合物（2.70g, 4.848mmol )，依實施例1 (7)之方法反應，可得標題化合物（3. 11 g,產率95%) 〇 IR vma “膜）3 5 04，2926，2 8 5 5，1 680 (w), 1 65 9 (w)，1464 cm—1. -135 - 200413400 400 MHz 】H NMR (CDC13) δ 0.04 (6H，s)，0.88 (9H, s), 0.8 8 -0.92 ( 1 5H, m，含 9H, s，at δ 0.90 ppm)，1.26 (3 6H，bs' 1.5 8 - 1.65 (7H，m)，2.71 (1H，d，J二2.2 Hz，〇H)，3.28 (ih， dd, J = 2.7，9.5 Hz), 3.5 2- 3.90 (9H，m)，5. 10 (1H，d, J = 3 7 Hz), 5.19 (1H，m)，6.19 (1H，dd, J = 2.2, 12.5 Hz). FABMS (陽離子）m/z，671 [M-H] +，693 [M + Na]+ (力口入 N al). H R F A B M S C 3 9 H 7 8 〇 6 S i N a 計算値·· 6 9 3.5 4 6 6。實測値： 693.5469. (5) (E) — 1—丙烯基4一〇一烯丙氧鑛基一 6—〇一 (第三丁二甲石夕院基）一2，3 —二一 0 —十二基—a— D — 吡喃葡糖苷（第A a 8工程）將（4 )所得化合物（3 · 1 〇 g，4 · 6 1 9 m m ο 1 )，依實施例1 (8 )之方法反應，可得標題化合物（3.49§，產率10〇% ) 〇 IR vmax(膜）2926，2856, 1 7 5 8，1 680 (w), 1661 (w)，1464 cm"1 . 400 MHz !H NMR (CDC13) δ 0.02 (3H, s), 0.03 (3H, s), 0.88 (9H, s), 0.88 (6H, t, 1 = 6.6 Hz), 1.25 (3 6H, bs), 1.51-1 57 (7H, 3.35 (1H, dd, 1 = 3.7, 9.7 Hz), 3.51-3.83 (8H, m)，4.62-4.65 (2H，m)，4.72 (1H，t，J二9.5 Hz), 5.10 (1H，d J = 3.7 Hz)，5.19 (1H，m)，5.26-5.39 (2H，m), 5.94 (1H，m), 6 · 1 8 ( 1 H，d d，J 二 1 . 5，1 2.5 H z). FABMS (陽離子）m/z，7 5 3 [M_H] +，7 7 7 [M+Na]+ (加入 200413400Hz, NH). FABMS (cation) m / z, 1 6 80 [M + Na] +. HRFABMS, C88H157N023 P2Na Calculated 値: 1 6 8 1.05. Measured fluorene: 1681.05. (14) Phosphonic acid group 6—O— {2 —deoxy—3—O— [(R) — 3 —methoxydecyl] —6—O—methyl—2— [(Z ) — 11- (octadecenyl) amino]] 4-10-phosphonic acid-β-D-glucopyranosyl} -3-0-dodecyl-2-0-[[R ) —3-Hydroxytetradecyl] -α-D-glucopyranoside (Project C5) The compound α-form (140 mg, 0.084 mmol) obtained in (13) is reacted according to the method of Example 1 (14). The title compound was obtained as a powder (45 mg, 40% yield). IR vmax (KBr) 3 2 8 9 (w), 3077 (w), 2924, 285 3, 1 627, 1 5 56, 1467 cm'1. 400 MHz NMR (CDCI3-CD3OD, 5: 1) δ 0.86- 0.90 (12H, m), 1.27 (66H, bs) 5 1.40-1.74 (12H, m), 1.97-2.02 (4H, m), 2.2 2-2.2 4 (2 H, m), 3 · 2 2-4 1 3 (2 6 H, m, including 2 3 H, sat 3. 3 0 and 3.40 ppm), 4.77 (1 H, d, J = 7.3 H z), 5. 3 5-5 · 3 9 ( 2 H, m), 5.7 2 (1 H, m). -132-200413400 FABMS (anion) m / z, 1328 [M-H]-, 1 350 [M + Na-2Hr. HRFABMS, C68H132N. 19P2 calculation: 1 3 2 8.8 8 7 1. Measured fluorene: 1 3 2 8.8 8 7 3. [Example 9] Glucosino group 6 — 0 — {2 —Deoxy-3 — 0 — [(R) — 3 -methoxydecyl] — 6-0 — Methyl-2-[(Z) — 11- (octadecylamino) amino] -4-10-phosphonic acid-β-D-glucopyranosyl 丨 -3—O-dodecyl -2-Ο — [(R) —3-Hydroxytetradecyl] -β-D-glucopyranoside (Project C a 5) _ The β-form (150 mg, 0.090 mmol) of the compound obtained in Example 8 (13) ) 'According to the method of Example 1 (14), the title compound (45 mg, yield 37%) was obtained as a powder. 400 MHz ln NMR (CDCI3-CD3OD, 5: 1) δ 0.88 (12Η, t, J = 6.6 Hz), 1.26 (66H, bs), 1.41-1.74 (12H, m), 2.00-2.04 (4H, m) , 2.24-2.28 (2H, m), 3.12-4 · 07 (26H, m, including two 3H, s at 3.30 and 3.40 ppm), 4.92-4.97 (2H? M), 5.34-5.3 6 (2H , m). Lu FABMS (anion) m / z, 1 328 [M-ΗΓ. C68H133N019P2 Analytical calculation 値: c, 61.38; H, 10.07; N, 1.05; P, 4.66 ° Measured 値: C, 61.00; H, 9.97; N, 1.12; P, 4.24. [Example 1 〇] Phosphonic acid group {2-deoxy-3-O — [(R) -methoxydecyl] -6-6 0-1 Methyl-2 — [(Z) —1 1- (octadecenyl) amino] —4 ~ 0—phosphonic acid group β-D—pyranosylglucose 丨 2,3 -dione Ο -133-200413400 Dodecyl-α-D-pyranoglucoside (1) Allyl 2,3-dioxoyl-12,6--0-isopropylidene-cx-D —Glucopyranoside (Project Aa 4) The obtained propyl 3 — 0 —dodecyl-4,6 — 0 —isopropylidene —α — D —pyranoglucoside obtained in Example 8 (3) will be used. Glycoside (2.90g, 1 · 14mmol), using alkane The chemical agent and bromododecane were reacted according to the method of Example 1 (4) to obtain the title compound (6.49 g, yield 98%) as a wax. 400 MHz NMR (CDC13) δ 0.88 (3H, t, J-6.6 Hz), 1.26 (36H, bs), 1.41 (3H, s), 1.48 (3H, s), 1.50- 1.60 (4H, m), 3.30 (1H, m), 3.49-3.74 (8H, m), 3.83 (1H, m)? 4.08 (1H, dd, J = 6.6, 13.3 Hz), 4.18 (1H, dd, J = 5. 1, 13.3 Hz ), 4.90 (1H, d, J = 3.7 Hz), 5.22 (1H, m), 5.32 (1H, m), 5.92 (1H, m) · (2) allyl 2,3-dione O-ten Diyl a-D-glucopyranoside (Project A a 5) The compound (6.4 0 g, 10.7 2 2 mm ο 1) obtained in (1) can be reacted according to the method of Example 1 (5). The title compound was obtained as a wax (2.6 2 g, yield 4 4%). IR vmax (KBr) 3 3 64 (br), 29 1 9, 2 850, 1 467 cm-1. 400 MHz 4 NMR (CDC13) δ 0 · 88 (6H, t, J = 6.6 Hz), 1.26 (36H, bs), 1.54-1.60 (4H, m), 1.95 (1H, t, J = 5.7 Hz, 0H), 2.46 (1H, d, J = 2.9 Hz, 0H), 3.28 (1H5 m) , 3.46-3.90 (8H, m), 3.9 3 (1H, m), 4.0 7 (1H, dd, J-6.6, 13.2 Hz), 4.20 (1H, dd, J = 5.], 13.2 H z) , 4.96 (1 H, d, J: 3. 7 H z) 5 · 2 1-5.3 5 (2 H, 200413400 m), 5.93 (1H, m). FABMS (cation) m / z, 5 5 5 [MH] '579 [M + Na] +. HRFABMS, C33H64〇Na calculated 値: 579.4600. Measured 57: 57 9.4 5 8 1. (3) (E) — 1-propanyl 2,3 — — ^-12-dodecyl-a—D —pyranoside (Project A a 6) (2) The obtained compound (2.60 g, 4.67 mm ο 1) was reacted according to the method of Example 1 (6) to obtain the title compound (2.60g, yield 100%). IR vmax (KBr) 3 34 1 (br), 2919, 2851, 1678 (w), 1468 cm-1. 400 MHz 4 NMR (CDC13) δ 0 · 88 (6H, t, J = 6.6 Hz), 1 · 26 (36H, bs), 1.55- 1.60 (9H, m), 1.89 (1H, bs, 0H), 2.50 (1H, m, 0H), 3.30 (1H, dd, J = 3.7, 8.8 Hz), 3.46-3 · 78 (6H, m), 3.7 0- 3.84 (2H, m), 3.93 (1H, m), 5.12 (1H, d, J 3.7 Hz), 5.19 (1H, qd, J = 6.6, 12.5 Hz), 6.18 (1H, dd, J 2 1.5, 12.5 Hz). FABMS (cation) m / z, 5 5 5 [MH] +, 579 [M + Na] + · (4) ( E) — 1 —propenyl 6 — 0 (third butadisilyl) — 2, 3 — 1 — 0 — undecyl — a — D-pyranoglucomannan (Project A a 7) The compound (2.70 g, 4.848 mmol) obtained in (3) was reacted according to the method of Example 1 (7) to obtain the title compound (3.11 g, yield 95%). IR vma "membrane" 3 5 04, 2926, 2 8 5 5, 1 680 (w), 1 65 9 (w), 1464 cm—1. -135-200413400 400 MHz] H NMR (CDC13) δ 0.04 (6H, s), 0.88 (9H, s ), 0.8 8 -0.92 (1 5H, m, including 9H, s, at δ 0.90 ppm), 1.26 (36H, bs' 1.5 8-1.65 (7H, m), 2.71 (1 H, d, J (2.2 Hz, 0H), 3.28 (ih, dd, J = 2.7, 9.5 Hz), 3.5 2-3.90 (9H, m), 5. 10 (1H, d, J = 3 7 Hz ), 5.19 (1H, m), 6.19 (1H, dd, J = 2.2, 12.5 Hz). FABMS (cation) m / z, 671 [MH] +, 693 [M + Na] + (force into N al ). HRFABMSC 3 9 H 7 8 〇6 S i N a Calculated ··· 6 9 3.5 4 6 6. Measured 値: 693.5469. (5) (E) — 1-propenyl 4-10 allyloxy One 6-0 (Third Dimethyl Shixianyuanji) One 2,3-Dione 0-12 Dodecyl-a-D-glucopyranoside (Project A a 8) The compound obtained by (4) (3 · 10 g, 4 · 6 19 mm ο 1), and reacted according to the method of Example 1 (8) to obtain the title compound (3.49 §, yield 100%) 〇IR vmax (membrane) 2926, 2856, 1 7 5 8, 1 680 (w), 1661 (w), 1464 cm " 1. 400 MHz! H NMR (CDC13) δ 0.02 (3H, s), 0.03 (3H, s), 0.88 (9H, s), 0.88 (6H, t, 1 = 6.6 Hz), 1.25 (3 6H, bs), 1.51-1 57 (7H, 3.35 (1H, dd, 1 = 3.7, 9.7 Hz), 3.51-3.83 (8H, m), 4.62-4.65 (2H, m), 4.72 (1H, t, J 9.5 Hz), 5.10 (1H, d J = 3.7 Hz), 5.19 (1H , M), 5.26-5.39 (2H, m), 5.94 (1H, m), 6 · 1 8 (1 H, dd, J 2 1.5, 1 2.5 H z). FABMS (cation) m / z, 7 5 3 [M_H] +, 7 7 7 [M + Na] + (added 200413400

Nal). HRFABMS C43H82〇8SiNa 計算値·· 777.5 67 7。實測値： 777.5 64 1. (6) 4 —〇一烯丙氧羰基—2，3—二—O —十二基—d -吡喃葡糖（第A a 1 0工程）將（5)之化合物（3.60g，4.7 67mm〇l)溶在二氯甲烷（ 10mL)及乙腈（20mL)，加入4 8 %氫氟酸水溶液（3 m L ) ，於室温下攪拌1 6小時，稀釋以乙酸甲酯。反應液以水，重碳酸鈉溶液及食鹽水洗，於硫酸鎂下乾燥。過濾濃縮後，以矽膠柱層析純化。溶離以乙酸乙酯，可得標題化合物 (2.12g，產率 74% )。 IR vmax(膜）3446 (br), 2920，285 1，1 754，1 724，1468 cm-1· 400 MHz 4 NMR (CDC13) 0·88 (6H，t，J二6·6 Hz)，1.25 (32H，bs)，1.43-1.58 (2H，m)，1.69 (1H，bs，〇H)，3.12-3.98 (7H, m), 4.65-4.72 (3H, m), 5.28-5.40 (2H, m), 5.93 (1H? m). FABMS (陽離子）m/z, 5 8 3，623 [M + Na] + . HRFABMS C34H64〇sNa 計算値：623.4499。實測値： 623.4490. (7) 6— 0 — {2—去氧一4— 0—二烯丙膦酸基一 3 —〇一〔（R) — 3 —甲氧癸基〕一6—0 —甲基一2— 〔（2，2，2 一三氯乙氧羰基）胺基〕一 β—D —卩比喃葡糖基}— 2，3—一一〇一十二基一 D —吡喃葡糖（第C c 1工程）將（6 ;所得化合物（2.6 5 g , 3 . 1 4 2 m m 〇 ])及二fe甲基亞 ^ 137 - 200413400 胺醯基2 -去氧—4 一 0 -二烯丙膦酸基—3 - Ο —〔（ R ) —3—甲氧癸基〕一6 —〇一甲基一2— 〔（2，2，2 —三氯乙氧羰基）胺基〕—D —吡喃葡糖苷（1.82g，3. 1 12mmol )( 美國專利第5,9 3 5,9 3 8號公報記載），依實施例1 ( 10 )之方法反應，可得標題化合物（3 . 8 6 g ,產率9 6 % )。 IR vmax(膜）3 500-3 1 00 (w), 2926，2856，1 7 5 3, 1736，1542 cm"1. 400 MHz ]H NMR (CDC13) 0.8 8 ( 9 H，t，J 二 6.6 H z)，1 · 2 6 (48H，bs)，1.43- 1.75 (6H, m), 3.1 1 -3.90 (24H, m), 4.13-4.40 (2H, m)? 4.55-4.85 (10H, m), 5.24-5.39 (6H, m), 5.89-5.99 (1H, m)· FABMS (陽離子）m/z, 1304，1302 [M + Na，35C1] + . HRFABMS C61H109Cl3N〇18PNa 計算値：1 3 0 2.6 3 4 6。實測値：1302.6333. (8) 4— 0 —烯丙氧羰基—6— 0 — {2-去氧—4 一 0 —二烯丙膦酸基一 3 — 〇—〔（R) — 3 —甲氧癸基〕一6— Ο —甲基一 2-〔（Ζ) - 11一（十八碳烯醯基）胺基〕一 β - D- 吡喃葡糖基丨一 2，3-二一 Ο —十二基—D-吡喃葡糖（第 C c 2工程）將（7 )所得化合物（1.90g，1.4 8 2mmol )，依實施例1 (1 1 )之方法反應，可得油狀標題化合物（1.32 g,產率 65% )。 IR v m ax (膜）3 3 02 (b r), 292 6，2 8 5 5，1 754，1 65 2，1 549，1465 200413400 400 MHz ]H NMR (CDC13) 0.8 8 ( 1 2 H，t，J = 6 · 6 H z )，1 · 2 6 (66H，bs)，1.40- 1.80 ( 1 0H，m)，1.99-2.02 (4H，m)，2.17-2.33 (2H, m), 3.10-4.10 (25H, m), 4.24-4.63 (8H5 m), 5.21-5.35 (8H，m)，5.8 7 -5.9 8 ( 3 H，m)，6.12 (1H，NH). FABMS (陽離子）m/z，1 3 92 [M + Na] + . HRFA.BMS，C76H140N〇17PNa 計算値：1 3 9 2.9 7 5 6。實測値： 1392.9774. (9)二烯丙膦酸基4一 O —烯丙氧羰基一6 —〇一{2 —去氧一 4 一 Ο —二烯丙膦酸基一3 — Ο—〔（R) — 3 —甲氧癸基〕一6 一 Ο —甲基—2 —〔（ Ζ ) — 11—（十八碳稀釀基）月女基〕—β— D —吡喃葡糖基丨一2，3 —二一 0 —十二基一 a— D 一吡喃葡糖苷及二烯丙膦酸基4一 0 —烯丙氧羰基一 6 - 0 — {2 —去氧一4 —〇一二烯丙膦酸基一 3— 0—〔（R) — 3—甲氧癸基〕一 6— 0 —甲基—2—〔（Ζ) - 11一（十八碳細釀基）胺基〕一 β - ϋ一吡喃葡糖基}一 2，3-二一 Ο —十二基一 β — D —吡喃葡糖苷（第C a 4工程）將（8 )所得化合物（1.32g, 0.963mmol ) ’依實施例1 (13 )之方法反應，可得標題化合物α體（3 5 6 mg，產率 25% )及β體（37 8 mg,產率26% )油狀物。 α體： IR vmax(膜）3310，3 0 8 5，2926，285 5，1 7 5 7，1 665，1 548， 1 4 6 5 cm-1. 4 0 0 Μ Η z 1 Η N M R ( C D C 13) δ 0.8 8 ( 1 2 Η，t，J = 6.6 H z )，1 . 2 6 (6 6 Η，b s), 1 . 4 0 - ] . 7 5 ( 1 0 Η，m), 1 · 9 9 - 2.0 】（4 Η，m )，2.2 1 - -139 - 200413400 2.25 (2H, m)，3.2 1 - 3.8 3 (22H，m，含 2 個 3H5 s，at 3.28 and 3.38 ppm), 3.96-4.02 (2H, m)，4.26 ( 1 H, dd, J = 9.6，18.3 Hz), 4.5 2-4.7 3 ( 1 1 H，m)，5.23 -5.42 ( 1 2H，m)，5.73 (1H，dd， J = 3.3，6.3 Hz), 5.87-6.01 (5H，m), 6.53 (1H, d，J二 8.1 Hz， NH). FABMS (陽離子）m/z，1 5 52 [M + Na] + . HRFABMS，C82H149N〇20P2Na 計算値：1553.0046。實測値：1 5 5 3.004 1 . β體： · IR vmax(膜）3 3 1 0, 308 6 (w), 2926，2855，1 7 57，1 66 8，1 549, 1 4 6 5 cm"1. 400 MHz lU NMR (CDC13) δ 0.88 (12H, t, 1 = 6.6 Hz), 1.26 (66H, bs)5 1.40- 1.7 5 ( 1 0H, m), 2.00-2.02 (4H? m), 2.20- 2.25 (2H，m), 3 . 1 8 - 3.7 5 (2 2 H，m，含 2 個 3 H，s，a t 3 · 2 7 a n d 3.38 ppm), 4.00 (1H, m), 4.25 (1H, m), 4.47-4.63 (11H, m), 4.70 (1H, d, J = 8.8 Hz), 4.95 (1 H，d d，J 二 5 . 1，8.1 Hz), 5.23- 5.43 (12H, m)，5.86-5.97 (5H，m)，7·48 (1H，d，J二9.5 Hz, · NH). FABMS (陽離子）m/z，1 5 52 [M + Na] + . HRFABMS，C82H149N〇20P2Na 計算値：1 5 5 3.0046。實測値 :1553.0040. (10)鱗酸基 6— Ο — {2 —去氧—3— Ο—〔（R) - 3 —甲氧癸基〕--6 - Ο -甲基—2 —〔（ Z ) - 1 1 一（十八碳烯醯基）胺基〕一 4一 Ο-膦酸基一 β-D-吡喃葡糖基丨一 2，3 -140- 200413400 一二一 0 -十二基一 α — D —吡喃葡糖苷（第C a 5工程）將（9 )所得化合物α體（153mg, 0· lOOmmol )，依實施例1 ( 1 4 )之方法反應，可得蠟狀之標題化合物（7 0 m g, 產率5 4 % )。 IR vmax (KBr) 3 292 (br), 3 294，2 8 5 3，1 6 3 0, 1 5 5 1, 1 467 cm-1 400 MHz 'H NMR (CDCI3-CD3OD, 4:1) δ 0.88 (12H, m), 1.27 (66H, bs), 1.40- 1.76 ( 10H, m), 1.96-2.04 (4H, m), 2.22-2.26 (2H，m)，3.23-4.1 0 (25H, m,含 2 個 3H，s at 3.30 and 3.40 ppm), 4.74 (1H，d，J = 8.3 Hz), 5.3 4 - 5.3 9 (2 H，m)， 5.64 (1H，m)· FABMS (陰離子）m/z, 1 284 [Μ-ΗΓ. HRFABMS，C66H128N〇i8P2 計算値·· 1 2 8 4.8 6 0 7。實測値： 1284.8605. C66H129N018P2 分析計算値：C，61.61; H，10.11; N，1.09; P， 4.81。實測値：C，61.94; H，9.61; N，1.17; P, 4.73. 〔實施例1 1〕膦酸基6— Ο— {2 —去氧一 3 —〇—〔（r) — 3 —甲氧癸基〕一6— Ο—甲基一 2—〔（z) — 11—（十八碳烯醯基）胺基〕一 4— Ο —膦酸基一 β— D—吡喃葡糖基丨一2，3 —二一〇一十二基一 β - D -吡喃葡糖苷（第c a 5工程）將實施例1 〇 ( 9 )所得化合物β體（！ § 5 m g，〇 . 1 2 1 m m ο 1 ) ，依實施例1. ( 1 4 )之方法反應，可得蠟狀之標題化合物 (1 0 6 m g，產率 6 8 % )。 -141 - 200413400 IR vmax(KBr) 3 3 87，3 299，2924, 28 5 3，1631，1 5 52, 1 46 7 cm- i 400 MHz ]H NMR (CDCl3-CD3〇D, 4:1) δ 0.89 (12H, m), 1 .27 (66H, bs), 1.40- 1.76 ( 1 OH, m), 2.00-2.04 (4H，m)， 2.25 -2.29 (2H, m)，3.1 卜 3.89 (2 3 H，m，含 2 個 3H，s at 3.31 and 3.4 1 ppm), 4.00-4.05 (2H, m), 4.94-4.98 (2H, m), 5.32-5.3 7 (2H, m)· FABMS (陰離子）m/z，1 284 [M-ΗΓ，1 3 06 [M + Na-2Hr. HRFABMS，C66H128N〇i8P2 計算値：1 2 8 4.8 6 0 7。實測値： 1284.8605. C66H129N〇18P2 分析計算値：C，61.61; H，10·1 1; N，1·09; P， 4.81。實測値：C，6 2 · 3 7 ; Η，9.5 6 ; N，1 . 1 8 ; P，3.9 6 · 〔實施例1 2〕膦酸基6— 0— {2 —去氧—3 — O—〔（R) — 3—甲氧癸基〕—6 - 〇 —甲基一 2—〔（Z) — 11—(十八碳烯醯基）胺基〕一4一〇一鱗酸基一 β— D — P比喃匍糖基}一3— Ο—十一基一 2_ ◦一十四基一 α—D —吡喃葡糖苷 (1)燃丙基3 — 0—十二基一 4’ 6— 0—亞異丙基—2— 〇一十四基一 a — D —吡喃葡糖苷（第A a 4工程）將實施例8 ( 3 )所得嫌丙基 3 — 0 —十二基一 4 ’ 6 - 0 一亞異丙基一 α—D—吡喃葡糖苷（3g，7 mmol)及1 一溴十四院（2 · 3 g，8.4 m m ο 1 )溶在D M F ( 2 5 m L )，力□入氫化鈉 (5 5 %油中，4 0 0 m g，8.3 m m 0 1 )。依實施例](〇之方法處理可得油狀目的化合物（3.7g，產率86%) ° 200413400 400 MHz ]Η NMR (CDC13) δ 0.88 (6H, t? J-6.6 Hz), 1.26 (40H，bs)，1.40 (3H，s)，1.47 (3H, s)，1.50-1.60 (4H，m)， 3.10-4.35 (12H，m)，4·37 (1H，d，J = 8.1 Hz)，5.17-5.34 (2H， m)，5 · 9 1 ( 1 H , m) · (2) 烯丙基3 —〇一十二基一 2— O —十四基一 a— d —毗喃葡糖苷（第A a 5工程）將（1 )所得化合物（1 . 9 m g，3 m m ο 1 )溶在 M e Ο Η ( 3 0 m L )，加入對甲苯磺酸（8〇mg)，於室温攪拌40分。將反應液減壓濃縮後，以乙酸乙酯稀釋。以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮後，進行$夕膨層析純化。溶離以環己烷一乙酸乙酯（1 : 1 )可得標題化合物（1 . 5 7 g，產率8 9 % )。 400 MHz 'Η NMR (CDC13) δ 0.88 (6H, t5 J = 6.6 Hz), 1.26 (36H，bs)，1.52- 1.62 (4H, m), 2.07 (1H, t, J = 6.6 Hz, OH), 2.46 (1H, d, 1 = 2.2 Hz, OH), 3.10-4.20 (12H, m), 4.38 (1H, t, 1 = 8.1 Hz), 4.91 (1H, d, J = 3.7 Hz), 5.21^.35 (2H, m), 5.92 (1H，m). (3) (E) — 1 一丙烯基3— O—十二基一 2— 〇-十四基一 α - D —吡喃葡糖苷（第A a 6工程）將（2 )所得化合物（1 .57g，2.68mmol )溶在thF ( 4 0mL )，加入氫活化之 Ir[C8H12(MePh2P)2]PF6 ( 5mg )，於室温下攪拌過夜。將反應液濃縮，可得標題化合物（ 1.2 g ,產率7 6 % )。所得標題化合物ij：其可使用於下一反 -143 - 200413400 400 MHz ]H NMR (CDC13) δ 0.88 (6H, t; J-6.6-7.3 Hz), 1.26(40H，bs)5 1.5 3 - 1.60 (7 H，m，含 3H，dd，J二 1.5, 7.3 Hz， at 1.56 ppm)，2.06 (1H，t，J二6.6 Hz，〇H)，2.44 (1H，d， j 二 1.5 Hz，〇H)，3.14-3.92 (10H，m)，4.52 (1H，d，J = 7.3 Hz), 5.12 (1H, m), 6.21 (1H, qd, J-1.5, 12.5 Hz). (4) (E) — 1 一丙烯基6—〇一（第三丁二甲矽烷基）一 3— 0—十二基一 2— 0 —十四基—a— D —吡喃葡糖苷（第 A a 7工程）將（3)所得化合物（1.2g，3.09mmol)溶在二甲基甲醯胺（40mL)，力□入第三丁二甲矽烷氯（ 558mg，0.384 mmol )及咪唑（5 25mg, 7.72mm〇l )，於室温下攪拌過夜。以矽膠柱層析純化。溶離以己烷一乙酸乙酯（5 : 1 )混合溶液，可得油狀標題化合物（1 . 5 g，產率9 0 % )。 400 MHz ]H NMR (CDC13) δ 0.08 (6Η, s), 0.86-0.90 ( 1 5Η, m，含 9H，s，at 0.89 ppm), 1.26 (4 0 H , b s )，1 · 5 3 - 1 . 6 0 (7 H， m)，3·02 (1H，d，J = 2.2 Hz，〇H)，3.13-3.24 (2H, m)，3.33 (1H，m)，3.49-3.89 (7H, m)，4.47 (1H，d，J二7.3 Hz)，5.11 (1H，m)，6.20 ( 1H, dd，J二 1.7，12.1 Hz). (5) (E)— 1—丙烯基4一〇一烯丙氧羰基—6— O—( 第三丁二甲矽烷基）一 3—0 —十二基一 2 - Ο—十四基一 α 一 D -毗喃葡糖苷（第A a 8工程）將（4)所得化合物（1.5g, 2.15mmol)溶在甲苯（30mL )，加入卩比D定（6 8 0 m g , 8.6 m m 0 1 )，於冰冷卻下加入光氣 (3 2 0 mg, 1.07mmol )，劇烈攪拌1 〇分。反應溶液中加入 -144 - 200413400 烯丙醇（1 . 2 4 g，2 1 . 3 m m ο 1 )，於冰冷卻下攪拌1小時。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗，於硫酸鎂下乾燥。過濾濃縮後，以矽膠柱層析純化。溶離以環己烷一乙酸乙酯（1 4 : 1 )，可得標題化合物（1 g，產率 8 3%)。 400 MHz NMR (CDC13) δ 0.03 (6H, s), 0.8 6 -0.89 ( 1 5H, m，含 9H，s，at 0.87 ppm)，1.25 (40H, bs)，1.51-1.56 (7H, m), 3.15 (1H, dd? J = 7.8, 9.9 Hz), 3.35 (1H? dd, J = 8.8, 9.9Nal). HRFABMS C43H82〇8SiNa Calculated 77.67.67. Measured Thallium: 777.5 64 1. (6) 4-O-allyloxycarbonyl-2,3-di-O-dodecyl-d-glucopyranose (Project A a 1 0) The compound (3.60 g, 4.7 67 mm) was dissolved in dichloromethane (10 mL) and acetonitrile (20 mL), 48% aqueous hydrofluoric acid solution (3 ml) was added, and the mixture was stirred at room temperature for 16 hours. Diluted with methyl acetate ester. The reaction solution was washed with water, sodium bicarbonate solution and brine, and dried over magnesium sulfate. After filtration and concentration, it was purified by silica gel column chromatography. Ethyl acetate was used to obtain the title compound (2.12 g, yield 74%). IR vmax (film) 3446 (br), 2920, 285 1, 1 754, 1 724, 1468 cm-1 · 400 MHz 4 NMR (CDC13) 0 · 88 (6H, t, J = 6.6 Hz), 1.25 (32H, bs), 1.43-1.58 (2H, m), 1.69 (1H, bs, 0H), 3.12-3.98 (7H, m), 4.65-4.72 (3H, m), 5.28-5.40 (2H, m ), 5.93 (1H? M). FABMS (cation) m / z, 5 8 3,623 [M + Na] +. HRFABMS C34H64 sNa Calculated 値: 623.4499. Measured rhenium: 623.4490. (7) 6-0 — {2—deoxy-4—0—diallylphosphonic acid group 3—〇 — [(R) — 3 —methoxydecyl] —6-0 — Methyl-2-[(2,2,2-trichloroethoxycarbonyl) amino] -β-D-pyranoglucosyl} -2,3-1102-dodecyl-D-pyridine Glucosamine (Cc1 Project) (6; the obtained compound (2.6 5 g, 3.12 mm)] and bis-femethylmethylene ^ 137-200413400 amino amidino 2-deoxy-4- 0-diallylphosphonic acid group -3-Ο-[(R) -3-methoxydecyl]-6-0-methyl-2-[(2,2,2-trichloroethoxycarbonyl) amine Group] -D-glucopyranoside (1.82g, 3.112mmol) (described in US Patent No. 5,9 3,5,98,8), and reacted according to the method of Example 1 (10) to obtain the title Compound (3.86 g, yield 96%). IR vmax (membrane) 3 500-3 1 00 (w), 2926, 2856, 1 7 5 3, 1736, 1542 cm " 1. 400 MHz] H NMR (CDC13) 0.8 8 (9 H, t, J 2 6.6 H z), 1 · 2 6 (48 H, bs), 1.43- 1.75 (6H, m), 3.1 1 -3.90 (24H, m), 4.13- 4.40 (2H, m)? 4.55-4.85 (1 0H, m), 5.24-5.39 (6H, m), 5.89-5.99 (1H, m) · FABMS (cation) m / z, 1304, 1302 [M + Na, 35C1] +. HRFABMS C61H109Cl3N〇18PNa Calculation 値: 1 3 0 2.6 3 4 6. Measured thallium: 1302.6333. (8) 4-0 —allyloxycarbonyl-6-0 — {2-deoxy-4 — 0 — diallylphosphonic acid 3 — 〇— [(R) — 3-methoxydecyl] — 6 — 0 —methyl — 2- [(Z) — 11 (octadecenyl) amino] — β-D-glucopyranosyl丨 2,3-Dioxo-dodecyl-D-glucopyranose (Project Cc 2) The compound obtained in (7) (1.90 g, 1.4 8 2 mmol) was used according to Example 1 (1 1) The reaction was carried out in this way to obtain the title compound (1.32 g, yield 65%). IR vm ax (membrane) 3 3 02 (br), 292 6, 2 8 5 5, 1 754, 1 65 2, 1 549 , 1465 200413400 400 MHz] H NMR (CDC13) 0.8 8 (1 2 H, t, J = 6 · 6 H z), 1 · 2 6 (66H, bs), 1.40-1.80 (1 0H, m), 1.99 -2.02 (4H, m), 2.17-2.33 (2H, m), 3.10-4.10 (25H, m), 4.24-4.63 (8H5 m), 5.21-5.35 (8H, m), 5.8 7 -5.9 8 (3 H, m), 6.12 (1H, NH). FABMS (cation) m / z, 1 3 92 [M + Na] +. HRFA.BMS, C76H140N017PNa Calculated 値: 1 3 9 2.9 7 5 6. Measured 139: 1392.9774. (9) diallylphosphonic acid group 4—O—allyloxycarbonyl group 6—〇— {2 —deoxy-4 10— diallylphosphonic acid group 3 — 0— [( R) — 3 —methoxydecyl] —6—10—methyl—2 — [(Z) — 11— (octadecyl alcohol) melamine] —β—D—glucopyranosyl 丨-2,3-dione-0-dodecyl-a-D-glucopyranoside and diallylphosphonic acid group 4-0-allyloxycarbonyl group 6-0-{2 -deoxy-4 -〇 Diallylphosphonic acid group 3-0 — [(R) —3-methoxydecyl] -6-0—methyl-2 — [(Z) -11- (octadecyl fine alcohol) amine Group] -β-fluorenyl-pyranoglucosyl} -2,3-di-10-dodecyl-β-D-glucopyranoside (Project C a 4) The compound (8) obtained (1.32 g , 0.963 mmol) 'According to the method of Example 1 (13), the title compound was obtained in the form of α-form (35.6 mg, yield 25%) and β-form (37 8 mg, yield 26%). Alpha body: IR vmax (film) 3310, 3 0 8 5, 2926, 285 5, 1 7 5 7, 1 665, 1 548, 1 4 6 5 cm-1. 4 0 0 Μ Η z 1 Η NMR (CDC 13) δ 0.8 8 (1 2 Η, t, J = 6.6 H z), 1. 2 6 (6 6 Η, bs), 1. 4 0-]. 7 5 (1 0 Η, m), 1 · 9 9-2.0】 (4 Η, m), 2.2 1--139-200413400 2.25 (2H, m), 3.2 1-3.8 3 (22H, m, including 2 3H5 s, at 3.28 and 3.38 ppm), 3.96 -4.02 (2H, m), 4.26 (1 H, dd, J = 9.6, 18.3 Hz), 4.5 2-4.7 3 (1 1 H, m), 5.23 -5.42 (1 2H, m), 5.73 (1H, dd, J = 3.3, 6.3 Hz), 5.87-6.01 (5H, m), 6.53 (1H, d, J = 8.1 Hz, NH). FABMS (cation) m / z, 1 5 52 [M + Na] + HRFABMS, C82H149N20P2Na Calculated 値: 1553.0046. Measured radon: 1 5 5 3.004 1. Β body: · IR vmax (membrane) 3 3 1 0, 308 6 (w), 2926, 2855, 1 7 57, 1 66 8, 1 549, 1 4 6 5 cm " 1.400 MHz lU NMR (CDC13) δ 0.88 (12H, t, 1 = 6.6 Hz), 1.26 (66H, bs) 5 1.40- 1.7 5 (1 0H, m), 2.00-2.02 (4H? M), 2.20 -2.25 (2H, m), 3. 1 8-3.7 5 (2 2 H, m, including 2 3 H, s, at 3 · 2 7 and 3.38 ppm), 4.00 (1H, m), 4.25 (1H , m), 4.47-4.63 (11H, m), 4.70 (1H, d, J = 8.8 Hz), 4.95 (1 H, dd, J 2: 5.1, 8.1 Hz), 5.23- 5.43 (12H, m) , 5.86-5.97 (5H, m), 7.48 (1H, d, J 9.5 Hz, · NH). FABMS (cation) m / z, 1 52 [M + Na] +. HRFABMS, C82H149N〇20P2Na Calculated 値: 1 5 5 3.0046. Measured fluorene: 1553.0040. (10) Scale acid group 6— 0 — {2 —deoxy — 3 — 0 — [(R)-3 —methoxydecyl]-6-0-methyl — 2 — [( Z)-1 1 mono (octadecenylamino) amino]-4-10-phosphonic acid-β-D-glucopyranosyl-1, 2, 3 -140- 200413400 one two one 0-ten Diyl-α-D-glucopyranoside (Project C a 5) The compound α-form (153 mg, 0.100 mmol) obtained in (9) was reacted according to the method of Example 1 (14) to obtain a waxy substance. The title compound (70 mg, 54% yield). IR vmax (KBr) 3 292 (br), 3 294, 2 8 5 3, 1 6 3 0, 1 5 5 1, 1 467 cm-1 400 MHz 'H NMR (CDCI3-CD3OD, 4: 1) δ 0.88 (12H, m), 1.27 (66H, bs), 1.40- 1.76 (10H, m), 1.96-2.04 (4H, m), 2.22-2.26 (2H, m), 3.23-4.1 0 (25H, m, incl. 2 3H, s at 3.30 and 3.40 ppm), 4.74 (1H, d, J = 8.3 Hz), 5.3 4-5.3 9 (2 H, m), 5.64 (1H, m) · FABMS (anion) m / z , 1 284 [Μ-ΗΓ. HRFABMS, C66H128N0i8P2 Calculate 値 · 1 2 8 4.8 6 0 7. Measured 値: 1284.8605. C66H129N018P2 Analytical calculation 値: C, 61.61; H, 10.11; N, 1.09; P, 4.81. Measured fluorene: C, 61.94; H, 9.61; N, 1.17; P, 4.73. [Example 1 1] Phosphonic acid group 6—O— {2 —deoxy—3—〇 — [(r) — 3 —A [Oxydecyl] -6-O-methyl-2-[(z) -11- (octadecenyl) amino] -4-O-phosphono-β-D-glucopyranosyl丨 2,3-dioxoyl-β-D-glucopyranoside (Project ca 5) The β-form of the compound obtained in Example 10 (9) (! § 5 mg, 0.1 2 1 mm ο 1) and reacted according to the method of Example 1. (1 4) to obtain the title compound (106 mg, yield 68%) as a wax. -141-200413400 IR vmax (KBr) 3 3 87, 3 299, 2924, 28 5 3, 1631, 1 5 52, 1 46 7 cm- i 400 MHz] H NMR (CDCl3-CD3〇D, 4: 1) δ 0.89 (12H, m), 1.27 (66H, bs), 1.40- 1.76 (1 OH, m), 2.00-2.04 (4H, m), 2.25 -2.29 (2H, m), 3.1, 3.89 (2 3 H, m, containing 2 3H, s at 3.31 and 3.4 1 ppm), 4.00-4.05 (2H, m), 4.94-4.98 (2H, m), 5.32-5.3 7 (2H, m) · FABMS (anion ) M / z, 1 284 [M-ΗΓ, 1 3 06 [M + Na-2Hr. HRFABMS, C66H128N0i8P2 Calculate 値: 1 2 8 4.8 6 0 7. Measured 値: 1284.8605. C66H129N18P2 Analytical calculation 値: C, 61.61; H, 10.1 1; N, 1.09; P, 4.81. Measured erbium: C, 6 2 · 3 7; erbium, 9.56; N, 1.1 8; P, 3.9 6 · [Example 1 2] Phosphonic acid group 6-0— {2—deoxy-3—O — [(R) —3-methoxydecyl] -6—O-methyl—2 — [(Z) —11— (octadecenyl) amino] —4—10—phosphonic acid— β—D—P Glucosyl} —3—O—undecyl — 2 — ◦ Tetradecyl — α —D —glucopyranoside (1) propyl 3 — 0 — dodecyl — 4 '6-0—isopropylidene-2— 〇. Tetradecyl—a—D—glucopyranoside (Project Aa 4) The propyl 3—0—twelve obtained in Example 8 (3) 4 ′ 6-0-isopropylidene-α-D-glucopyranoside (3 g, 7 mmol) and 1-bromo tetramethylene (2 · 3 g, 8.4 mm ο 1) were dissolved in DMF (2 5 m L), force into sodium hydride (55% oil, 400 mg, 8.3 mm 0 1). According to the example] (O method, the target compound was obtained as an oil (3.7 g, yield 86%) ° 200413400 400 MHz] Η NMR (CDC13) δ 0.88 (6H, t? J-6.6 Hz), 1.26 (40H , Bs), 1.40 (3H, s), 1.47 (3H, s), 1.50-1.60 (4H, m), 3.10-4.35 (12H, m), 4.37 (1H, d, J = 8.1 Hz), 5.17-5.34 (2H, m), 5 · 9 1 (1 H, m) · (2) allyl 3-12-dodecyl- 2-O-tetradecyl-a-d-pyranoglucoside (Section A a5) Dissolve the compound obtained in (1) (1.9 mg, 3 mm ο 1) in Me 3 3 (30 m L), add p-toluenesulfonic acid (80 mg), and leave it at room temperature. Stir for 40 minutes. The reaction solution was concentrated under reduced pressure, and then diluted with ethyl acetate. It was washed with sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration and concentration, it was purified by chromatography. Hexane-ethyl acetate (1: 1) gave the title compound (1.57 g, yield 89%). 400 MHz 'Η NMR (CDC13) δ 0.88 (6H, t5 J = 6.6 Hz), 1.26 (36H, bs), 1.52- 1.62 (4H, m), 2.07 (1H, t, J = 6.6 Hz, OH), 2.46 (1H, d, 1 = 2.2 Hz, OH), 3.10-4.20 (12H, m ) , 4.38 (1H, t, 1 = 8.1 Hz), 4.91 (1H, d, J = 3.7 Hz), 5.21 ^ .35 (2H, m), 5.92 (1H, m). (3) (E) — 1 Monopropenyl 3-O-dodecyl-2-0-tetradecyl-α-D-glucopyranoside (Project A a 6) The compound (2) obtained in (2) was dissolved in 1.57 g, 2.68 mmol thF (40 mL), hydrogen-activated Ir [C8H12 (MePh2P) 2] PF6 (5 mg) was added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated to obtain the title compound (1.2 g, yield 76%). The obtained Title compound ij: which can be used in the next trans-143-200413400 400 MHz] H NMR (CDC13) δ 0.88 (6H, t; J-6.6-7.3 Hz), 1.26 (40H, bs) 5 1.5 3-1.60 ( 7 H, m, containing 3H, dd, J (1.5, 7.3 Hz, at 1.56 ppm), 2.06 (1H, t, J: 6.6 Hz, 0H), 2.44 (1H, d, j, 1.5 Hz, 0H) ), 3.14-3.92 (10H, m), 4.52 (1H, d, J = 7.3 Hz), 5.12 (1H, m), 6.21 (1H, qd, J-1.5, 12.5 Hz). (4) (E) — 1-propenyl 6-0 (third butadisilyl) — 3—0—dodecyl — 2 — 0 —tetradecyl —a — D —glucopyranoside (Project A a 7) The compound obtained in (3) (1.2 g, 3.09 (mmol) was dissolved in dimethylformamide (40 mL), and tertiary butanesilyl chloride (558 mg, 0.384 mmol) and imidazole (525 mg, 7.72 mmol) were vigorously added, and the mixture was stirred at room temperature overnight. Purified by silica gel column chromatography. The mixed solution was dissolved in hexane-ethyl acetate (5: 1) to obtain the title compound (1.5 g, yield 90%) as an oil. 400 MHz] H NMR (CDC13) δ 0.08 (6Η, s), 0.86-0.90 (1 5Η, m, including 9H, s, at 0.89 ppm), 1.26 (4 0 H, bs), 1 · 5 3-1 6 0 (7 H, m), 3.02 (1H, d, J = 2.2 Hz, 0H), 3.13-3.24 (2H, m), 3.33 (1H, m), 3.49-3.89 (7H, m ), 4.47 (1H, d, J, 7.3 Hz), 5.11 (1H, m), 6.20 (1H, dd, J, 1.7, 12.1 Hz). (5) (E) —1-propenyl 4-101 Allyloxycarbonyl-6-O- (tertiary butanesilyl)-3-0-dodecyl-2-0-tetradecyl-α-D-pyranoglucoside (Project A a 8) The compound obtained in (4) (1.5 g, 2.15 mmol) was dissolved in toluene (30 mL), and the pyridine (6 80 mg, 8.6 mm 0 1) was added, and phosgene (3 2 0 mg, 1.07 mmol), and stirred vigorously for 10 minutes. To the reaction solution was added -144-200413400 allyl alcohol (1.24 g, 2 1.3 mm m ο 1), and the mixture was stirred under ice-cooling for 1 hour. The reaction solution was diluted with ethyl acetate, washed with sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration and concentration, purification was performed by silica gel column chromatography. Dissolution Using cyclohexane-ethyl acetate (14: 1), the title compound (1 g, yield 83%) was obtained. 400 MHz NMR (CDC13) δ 0.03 (6H, s), 0.8 6 -0.89 (1 5H, m, including 9H, s, at 0.87 ppm), 1.25 (40H, bs), 1.51-1.56 (7H, m), 3.15 (1H? Dd? J = 7.8, 9.9 Hz), 3.35 (1H? Dd, J = 8.8, 9.9

Hz), 3.43 (1H? m), 3.52-4.0 (7H, m), 4.6-4.75 (4H, m), _ 5.28-5.4 (3H, m), 5.9-6.0 (1H, m). (6) 4— O-燃丙氧羰基一3 — O—十二基—2 — 〇—十四基一 D —吡喃葡糖（第A a 1 0工程）將（5 )所得化合物（1 · 7 g )溶在二氯甲烷（1 3 mL )及乙腈（25mL )，加入矽膠粉（3 80mg )及48%氫氟酸水溶液 (1 mL )，於室温下攪拌1 6小時，以二氯甲烷稀釋。以重碳酸鈉溶液及食鹽水洗，於硫酸鎂下乾燥。過濾濃縮後，以矽膠柱層析純化。溶離以環己烷-乙酸乙酯（1 : 1 )，可得 _ 標題化合物（1 g，產率8 0 % )。 400 MHz NMR (CDC13) δ 0.86 (6H, t, J = 6.6 Hz), 1.26 (40H，bs)，1.50- 1.60 (4H，m)，3.12-4.0 (9H，m)，5.3-5.40 (3H，m)，5.90-5.95 (1H，m). (7) 4— O — j：希丙氧簾基一 6 —〇一{2—去氧一4 —〇—二烯丙膦酸基一 3 — Ο —〔（ R ) — 3 —甲氧癸基〕一 6 — 〇 —甲基一2— 〔（2，2，2—三氯乙氧羰基）胺基〕一 β— d — 1肚 200413400 喃葡糖基丨一 3— 0 —十二基—2— ◦一十四基—D—毗喃葡糖 (第C c 1工程）將（6 )所得化合物（6 5 4 m g，1 m m ο 1 )及三氯甲基亞胺醯基2 —去氧一 4— 0-二燒丙膦酸基—3— 0—〔（R) — 3- 甲氧癸基〕一6—〇一甲基一D—毗喃葡糖苷（84 3 mg, lmmol )(已知化合物：美國專利第5，9 3 5,9 3 8號）溶在 CH2C12 ( 30mL)，力口入 A g 〇 Tf ( 3 8 5 m g，1 . 5 m m ο 1 )，於氮氣下及於室温下攪拌l小時。反應液以二氯甲烷稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮，進行矽膠層析純化。溶離以己烷-乙酸乙酯（2 : 1 )，可得膠狀標題化合物（870mg，產率60% )。 400 MHz NMR (CDC13) δ 0.88 (9H? t, J = 6.6 Hz), 1.25 (52H，bs)，1.43- 1.77 (6H，m，含 3H，dd, J=1.5，6.6 Hz at 1.55 ppm), 3.21(1H, m), 3.28 (3H, s)5 3.3 2 ( 1 H, dd, J = 3.7, 9.5 Hz), 3.39 (3H, s), 3.45 -3.80 ( 1 5H, m), 4.5-4.7 (12H, m), 5.2-5.4 (6H,m), (1H, m), 5.89-5.98 (3H, m). (8) 4 —〇一烯丙氧羰基一 6— 0— {2 —去氧一4— 〇—二烯丙膦酸基一 3— Ο—〔（R) — 3 —甲氧癸基〕—6— 〇 —甲基一 2—〔（Ζ) - 11 一（十八碳烯醯基）胺基〕一 β— D- 吡喃葡糖基}— 3—0 —十二基一 2— Ο—十四基一 D —吡喃葡糖（第C c 2工程）將（7 )所得化合物（760mg，〇.58mmol )溶在THF ( 2 1mL )及乙酸（14mL )，加入鋅（7 8 0 m g)，劇烈攪拌3小時。將反應液過濾濃縮，以乙酸乙酯稀釋，以重碳酸鈉溶 -146 - 200413400 液及飽和食鹽水洗浄’於硫酸鎂下乾燥。過濾濃縮，所得一級胺溶在T H F ( 4mL )。加入含重碳酸鈉（1 1 2 m g )之水（2 m L )及1 1 一十八希酸之醯氯（2 3 0 m g，0 · 8 0 3 m m ο 1 ) 之T H F ( 4mL )溶液，於室温劇烈攪拌2小時。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄’於硫酸鎂下乾燥。過濾濃縮’進行矽膠層析純化。溶離以己烷一乙酸乙酯（1 : 1 )，可得膠狀標題化合物（700mg，產率8 6 % )。 400 MHz 4 NMR (CDC13) δ 0.88 (12H，t，J二 6.6 Hz)，1.25 (70H, bs), 1.40-1.80 (10H, m), 1.83-2.02 (4H, m), 2.17-2.22 (2H，m)，2.33 (1H，m)，3.10-3.36 (6H, m，含 3H, s, at 3.27 ppm)，3.38 (3H，s)，3.45-3.80 ( 1 2H，m)，3.81-4.10 (4H，m)，4.24-4.64 (8H，m)，5.2-5.4 (8H，m)，5.87-5.98 (3H，ni)，6.10 (1H，m)· (9)二;(¾丙膦酸基4一 O-稀丙氧羯基—6— O - {2-去氧一 4— Ο—二烯丙膦酸基一3 一0一〔（R) 一 3 一甲氧癸基〕一 6— 〇—甲基一 2—〔（Z) — 11一（十八碳燒醯基）胺基〕—β一 D —吡喃葡糖基丨一 3 — Ο—十二基一 2— 0—十四基一 α — D —吡喃葡糖苷（α體）及二烯丙膦酸基 4 一 0 — 烯丙氧羰基一6— 0 — {2 —去氧一 4 —〇一二烯丙膦酸基一 3 —〇—〔（R) — 3 —甲氧癸基〕一〇 —甲基一 2— 〔（Ζ )一 1 1 一（十八碳烯醯基）胺基〕一 β — D —毗喃葡糖基} 一 3 — 〇一十二基一 2 —〇一十四基—β — D — β 比喃葡糖甘1 ( β骨豆 )(第C a 4工程） 147 - 200413400 將（8 )所得化合物（6 80mg，0.48 6mmol )溶在二氯甲烷 (1 2 m L ) ’ 力口入 Na2S〇4 ( 1.5g) ， 1H -四〇坐（142mg, 2 m m ο 1 )及二異丙胺基磷酸二烯丙酯（1 5 5 m g，0.6 3 mm ο 1 ) ，於氮氣及室温下攪拌3 0分，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（1 : 1 )可得定量油狀之亞磷酸酯。將所得亞磷酸酯溶在THF ( 25mL)，加入30%過氧化氫水（ 5 0 0 m g，4,4 1 m m ο 1 )，於冰冷卻下攪拌3 0分。將反應液以乙酸乙酯稀釋，以1 0 %硫代硫酸水及食鹽水洗，於硫酸鎂下乾燥。過濾濃縮，進行矽膠層析純化。溶離以己烷-乙酸乙酯（1 : 1 )後溶離以乙酸乙酯，可得油狀標題化合物 α 體（200mg，產率 27%)及 β 體（220mg，產率 30%)。 α體： 400 MHz 】H NMR (CDC13) δ 0·88 (12Η，t, J = 6.6 Ηζ)，1.26 (70H, bs), 1.40-1.73 (10H, m), 2.00-2.05 (4H, m), 2.21- 2.25 (2H，m)，3.22-3.8 3 (22H，m，含 2 個 3H，s，at 3.28 and 3.38 ppm), 3.96-4.02 (2H, m), 4.25 (1H? m), 4.54-4.73 (11H，m)，5.23-5.40 ( 1 2H，m)，5.72 (1H，dd，J 二3.3，6.2 Hz), 5.89-5.99 (5H，m)，6.50 (1H，d，J = 8.1 Hz，NH). β體： 400 MHz 4 NMR (CDC13) δ 0·88 (12H，t，J二6.6 Hz)，ι·26 (70H，bs),1.40- 1.75 ( 1 0H，m)，2.00-2.02(4H，m)，2.1〇- 2.24 (2H，m)，3.1 8-3.80 (22H，m，含 2 個 3H，s，at 3.27 and 3 · 3 8 ρ p m)，4.0 0 ( 1 H , m), 4.2 5 ( ] H , m)，4 · 5 6 - 4.6 3 ( 1 1 H，m)， 4.7 0 ( 1 H，d，J 二 8.8 H z )，4.9 5 ( 1 H，d，；!二 5 . 1，8 . 1 H z )，5 . 1 3 200413400 (1H，d，J = 8.1 Hz)，5.23-5.43 (12H，m)，5.86-5.99 (5H，m)， 7.50 (1H, d, J = 9.5 Hz, NH). (10)膦酸基 6— 〇— {2 —去氧一3 —〇一〔(R ) — 3 —甲氧癸基〕一6—0 —甲基一 2—〔（Z) — 11 -（十八碳烯醯基）胺基〕一 4一 0 —膦酸基一 β — D —吡喃葡糖基丨一 3 —〇一十二基一2— Ο—十四基一 α— D —吡喃葡糖苷（第C a 5 工程）將（9 )所得化合物α體（200mg，0.055mm〇l )溶在THF (1 5 mL )，加入三苯膦（35mg，0.13 mmol)，三乙胺（ 1 3 5 m g , 1.33 mmol )，甲酸（120mg，2.6mmol)及 Pd(PPh3)4 ( 3 5mg，0.0 3mmol )，於氮氣及 5 5 °C 攪拌 2 0 小時。將反應液過濾後濃縮，以DEAE-纖維素8 g柱精製。溶離以 CHCl3-Me〇H-H2〇（2:3:1)之 0.05mol/L Ac〇.NH4 溶液可得含目的物之部份。收集部份與CHCl3-Me0H-H20 (1 : 1 : 1)之混合物，加入CHC13及〇· 15mol/L鹽酸水，於分液漏斗中攪拌，收集下層CHC13層並濃縮，可得鱲狀之標遍化合物（lOOmg，産率57%)。 400 MHz 4 NMR (CDC13-CD3〇D，4:1) δ 0.89 (12H，m)， 1.27 (70H, bs), 1.40- 1.80 ( 1 0H, m), 2.01-2.03 (4H, m), 2.24-2.26 (2H，m)，3.1 4- 3.92 (2 3 H，m,含 2 個 3H，s，at 3.30 and 3.40 ppm)，3.92-4.11 (2H，m)，4.72 (1H，d，J = 8.8 Hz), 5.34- 5.3 9 (2H，m)，5.63 (1H，m). FABMS (陰離子）m/z，]3i2 [Μ-ΗΓ. c 6 6 Η 1 2 9 N O i 8 P 2 分析計算値：c，6 0.0 0 ; H，1 0.2 3 ; N，1 . 〇 3 ; P， 200413400 4 · 5 5 ° 實測値：C，6 0.3 9 ; Η，9.9 1 ; N，1.2 8 ; P，3.8 6 . 〔實施例1 3〕膦酸氧基）乙基6 — 〇一 {2 —去氧一 4 —〇一膦酸基—3 —0〜[(R)— 3 —甲氧癸基]—6— 0 —甲基一2— 〔（Ζ) — 11 一（十八碳烯醯基）胺基〕一 β 一 D -吡喃葡糖基} 一 2，3 —二一〇—十二基一 α一 D-吡喃葡糖苷 (1) 烯丙基4，6 - 0 —亞異丙基一 a— D-吡喃葡糖苷（第A c 1工程）將 D - 葡萄糖（5g，22.7mmol )溶於 D M F ( 1 5mL )，加入2，2-二甲氧丙烷（15mL)及p-Ts〇H (200mg)，於室温下攪拌1 6小時。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥，過濾濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（4 : 1 一 2 : 1 )可得油狀標題化合物（3g,產率50%)。 400 MHz !H NMR (CDC13) δ 1.45 (3H,s), 1.52 (3H,s), 2.3 (1H, d, J=10.3 Hz, OH), 2.79 (1H? d, 2.2 Hz, OH), 3.51-3·88 (6H，m)，4.03 (1H，m)，4.23 (1H，m), 4.92 (1H，d， J = 3.7 Hz)，5.23-5.34 (2H，ni)，5.91 (1H, m). (2) 烯丙基2,3—二〜〇 —十二基一 4，6— 〇一亞異丙基一 α - D -吡喃葡糖苷（第a c 2工程）將（1 )所得化合物（5.4 g , 2 0.7 m m ο 1 )及1 —碘十二院 (14,7g，49.6mmol )溶在 DMF ( 3mL )，加入氫化鈉（ 5 5 %油中，2，4 g，4 9.6 m m ο 1 )，於室温下攪拌過夜。於冰冷卻下加入甲醇以分解氫化鈉。反應液以乙酸乙酯稀釋，以 150 200413400 水及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾後濃縮，進行砂膠層析純化。溶離以己烷一乙酸乙酯（9 : 1 )可得油狀標題化合物（7.4 g，產率6 〇 % 。 400 MHz ]H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (36H，bs)，1.41 (3H，s)，148 (3H, s), 1.50-1.60 (4H，m)， 3.49-3·73 (8H，m)，3.83 (1H，m)，4.08 (1H，dd，J = 6.6, 13.5 Hz), 4.18 (1H，dd，J 二5.1，3.3 Hz)，4.9 (1H，d，J = 3.7 Hz)， 5.22 (1H，m)，5.32 (1H，m)，5·92 (1H, m). (3) 2 —羥乙基2，3-二—〇—十二基—4，6 —〇一亞異丙基一 α - D—吡喃葡糖苷（第a bl工程）將（2 )所得化合物（4g，6.7mol )溶在THF- H20 ( 7 : 2，66mL)，加入過碘酸鈉（6.7g)及2.5%四氧化鎢之第三丁醇（1.4mL)溶液，於室温下攪拌2小時後，以乙酸乙酯稀釋。以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮可得醛殘渣。溶在乙醇（50mL )，加入硼氫化鈉（270mg )，攪拌20分後，加入乙酸，以乙酸乙酯稀釋。以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾後濃縮，進行矽膠層析純化。溶離以己烷-乙酸乙酯（3 : 1 )可得標題化合物（4 4 8 m g，產率4 1 % )油狀物〇 400 MHz NMR (CDC13) δ 0.88 (9Η, t, J-6.6 Hz), 1.26 (36H, bs), 1 .40 (3H，s)，1.41-1.43 (4H，m)，ΐ·48 (3H，s)， 2.82 (1H，bs，〇H)，3.30 (1H，m), 3.5 1-3.85 (i4H，m)，4.89 (1 H，d，J = 3 . 7 H z ) · -151 - 200413400 (4 ) 2〜（二烯丙膦酸氧基）乙基2，3 —二—〇一十二基一 4 ’ 6 — 0 —亞異丙基一 α — D —吡喃葡糖苷（第a b 2工程）將（3 )所得化合物（5.65 g，9.2 mmol )溶在二氯甲烷（ 7 0 m L ) ’力[]入 1H — 四口坐（1.54g，22mmol)，二異丙胺基磷酸一細丙醋（3.5 g，1 · 1 3 m m ο 1 )及硫酸鈉（6 g )，於室温下攪拌30分。加入THF(70mL)及31%過氧化氫水（2g )，於室温攪拌1 5分。將反應溶液以乙酸乙酯稀釋，以 1 0 % N a 2 S 2 0 3水溶液，重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾後濃縮，進行矽膠層析純化。溶離以環己烷一乙酸乙酯（2 : 1 )，可得標題化合物（6.6g,產率 9 9 % )。 400 MHz NMR (CDC13) δ 0.88 (6H, 1 = 6.6 Hz), 1.21-1.38 (36H, m), 1.39 (3H, s), 1.47 (3H,s), 1.5 0 - 1 . 5 8 (4 H , m), 3.25-3.30 (1H, m), 3.51-3.88 (11H, m), 4.23-4.27 (2H, m), 4.56-4.60 (4H, m), 4.89 (1H，d，J二3·7 Hz)，5.25-5.41 (4H，m)， 5.91-6.00 (2H, m). (5 ) 2—（二烯丙膦酸氧基）乙基一 2,3—二一 O—十二基一 a— D—吡喃葡糖苷（第A b3工程）將（4 )所得化合物（6.6g，9· lmmol )溶在 MeOH ( 60mL )，加入p — TsOH ( 4 12mg )，於室温下攪拌2小時後，濃縮，進行矽膠層析純化。溶離以乙酸乙酯，再溶離以含 j 0% MeOH之乙酸乙酯溶液，可得蠟狀之標題化合物（6g，產率96% )。 -]52 - 200413400 400 MHz ]H NMR (CDC13) δ 0.88 (6H, t, J-6.6 Hz), 1.26 (36H，bs)，1.5 0-1.71 (4H，m), 3.27 (1H, dd，J = 3.7，8.8 Hz)， 3.41-3.91 (11H, m)，4.24-4.28 (2H，m)，4.48-4.59 (4H, m)， 4.95 (1H，d，J = 3.7 Hz)，5.19-5.40 (4H，m), 5·90-6·00 (2H, m ). (6) 2—(二稀丙鱗酸氧基）乙基6—0— {2 —去氧一4 —〇一二烯丙膦酸基一3 —〇一〔（R) — 3—甲氧癸基〕一 6 —〇一甲基一2—〔（2，2，2 —二氯乙氧羰基）胺基〕一β— D — 吡喃葡糖基} 一 2，3 —二一 Ο -十二基—α — D -吡喃葡糖苷 (第C b 1工程）將三氯甲基亞胺醯基2-去氧一 4一 0-二烯丙膦酸基一 3 —〇一〔（R) — 3 —甲氧癸基〕一6— 0 —甲基一2— 〔（2， 2，2—三氯乙氧羰基）胺基〕一 α - D-吡喃葡糖苷（lg, 1 . 18mmol )(已知化合物，美國專利第5，9 3 5，9 3 8號）及（5 )所得化合物（1 · 0 2 g，1.4 9 m m ο 1 )溶在二氯甲院（ 3〇mL )，力口入分子篩 4 A ( 1 .5mg ) ，AgOTf ( 3 5 Omg， 1.36mmol)及 TMS 〇Tf ( 20mg, 0.090mmol )，於氮氣及室温攬拌過夜。將反應溶液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾後濃縮’進行矽膠層析純化。溶離以乙酸乙酯，再溶離以含5 % MeO Η 之乙酸乙酯溶液可得膠狀標題化合物（lg,產率60%)。 400 MHz ]H NMR (CDC13) δ 0.88 (9Η, t, 1 = 6.6 Hz), 1.26 (48H，bs)，1.3 8- 1.46 (2H，m), 1.5 3 - 1.5 8 (4H，ηι)，1.69-1.77 (2 H : m)，2.6 ( 1 H，b s，〇 H )，3 · 2 1 - 3 . 8 9 (2 3 H，m，含 2 個 3 H，s， -153 - 200413400 at 3,28 and 3.39 ppm), 4.09-4.3 2 (4H? m), 4.5 2-4.60 (8H, m)? 4-95 (1H? d, J = 3.7 Hz), 5.24-5.40 (8H, m), 5.89-5.99 (4H，1T1)，6.41 (1H，寬，NH)· (?) 2—(二烯丙膦酸氧基）乙基6 —〇一{2—去氧一4 —〇一少布丙膦酸基一 3 — Ο—〔（R) — 3 —甲氧癸基〕—6 —〇一甲基〜2一〔（z) — 11 一（十八碳烯醯基）胺基〕—β — D —吡喃葡糖基丨—2，3 —二一 Ο —十二基一 a— D —吡喃蔔糖苷（第C b 2工程）將（6)所得化合物（500mg，0.35mmol)溶在THF — 乙酸（3: 2，15mL)，加入鋅粉末（470mg，7.18mmol)，於室温下攪拌4小時。將反應液過濾後濃縮，以乙酸乙酯稀釋’以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾後濃縮，將所得一級胺溶在T H F ( 3mL )。加入含重碳酸鈉（124mg)之水（〇.9mL)及順—十八烯酸之醯氯（200mg，0.72mmol)之 T H F ( 1.5mL)溶液，於室温劇烈攪拌2小時。反應液以乙酸乙酯稀釋，以重碳酸鈉溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。過濾後濃縮，進行矽膠層析純化。溶離以乙酸乙酯，再溶離以含5 % MeOH之乙酸乙酯溶液，可得膠狀標題化合物（ 400mg,產率 7 5 % )。 400 MHz 'H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (66H，bs)，1.40- 1.7 9 ( 1 0H，ni)，1.99-2.04 (4H，m)，2.17_ 2·25 (2H，m)，3.0 1(1H，bs，〇H)，3.1 7 - 3.8 2 ( 24H, m,含 2 個 3 Η , s , at 3.28 a n d 3.38 p p ni), 3.97-4.31 ( 5 H，m )，4.5 2 - 4 · 5 8Hz), 3.43 (1H? M), 3.52-4.0 (7H, m), 4.6-4.75 (4H, m), _ 5.28-5.4 (3H, m), 5.9-6.0 (1H, m). (6) 4-O-propanecarbonyl- 3-O-dodecyl-2-0-tetradecyl-D-glucopyranose (Project A a 1 0) The compound obtained in (5) (1.7 g ) Dissolved in dichloromethane (13 mL) and acetonitrile (25mL), added silica gel powder (3 80mg) and 48% aqueous hydrofluoric acid solution (1mL), stirred at room temperature for 16 hours, and diluted with dichloromethane. It was washed with sodium bicarbonate solution and brine, and dried over magnesium sulfate. After filtration and concentration, the residue was purified by silica gel column chromatography. Dissolved in cyclohexane-ethyl acetate (1: 1) to obtain the title compound (1 g, yield 80%). 400 MHz NMR (CDC13) δ 0.86 (6H, t, J = 6.6 Hz), 1.26 (40H, bs), 1.50-1.60 (4H, m), 3.12-4.0 (9H, m), 5.3-5.40 (3H, m), 5.90-5.95 (1H, m). (7) 4—O—j: glycidyl-6—0— {2—deoxy—4—0—diallylphosphonic acid—3— 〇 — [(R) — 3 -methoxydecyl] -6 — 0—methyl-1 2-[(2,2,2-trichloroethoxycarbonyl) amino] -β-d-1 120042004400 Glucosyl 丨 One 3—0—Dodecyl—2— ◦ Tetradecyl—D—Pyranose (Project C c 1) The compound (6) obtained (6 5 4 mg, 1 mm ο 1 ) And trichloromethyliminofluorenyl 2-deoxy- 4-0-dithiopropionate-3-0- [(R) — 3-methoxydecyl] -6-methyl-1 D-glucopyranoside (84 3 mg, 1 mmol) (known compound: US Patent No. 5, 9 3 5, 9 3 8) was dissolved in CH2C12 (30 mL), and A g 〇Tf (3 8 5 mg, 1.5 mm ο 1), stirred under nitrogen at room temperature for 1 hour. The reaction solution was diluted with dichloromethane, washed with sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated, and purified by silica gel chromatography. Dissolve in hexane-ethyl acetate (2: 1) to obtain the title compound (870 mg, yield 60%) as a gel. 400 MHz NMR (CDC13) δ 0.88 (9H? T, J = 6.6 Hz), 1.25 (52H, bs), 1.43- 1.77 (6H, m, including 3H, dd, J = 1.5, 6.6 Hz at 1.55 ppm), 3.21 (1H, m), 3.28 (3H, s) 5 3.3 2 (1 H, dd, J = 3.7, 9.5 Hz), 3.39 (3H, s), 3.45 -3.80 (1 5H, m), 4.5-4.7 (12H, m), 5.2-5.4 (6H, m), (1H, m), 5.89-5.98 (3H, m). (8) 4-0-allyloxycarbonyl-6-0- {2-go Oxy 4-0-diallylphosphonic acid group 3-0-[(R) -3-methoxydecyl] -6-0-methyl-1 2-[(Z) -11 one (octadecyl Alkenyl) amino] -β-D-glucopyranosyl} —3-0—dodecyl-2—O—tetradecyl-D-glucopyranose (Cc 2 Project) will ( 7) The obtained compound (760 mg, 0.58 mmol) was dissolved in THF (21 mL) and acetic acid (14 mL), and zinc (780 mg) was added, followed by vigorous stirring for 3 hours. The reaction solution was concentrated by filtration, diluted with ethyl acetate, washed with a solution of sodium bicarbonate -146-200413400 and saturated brine, and dried over magnesium sulfate. The solution was concentrated by filtration, and the obtained primary amine was dissolved in THF (4 mL). Add a solution of sodium bicarbonate (112 mg) in water (2 ml) and 1 1 octadecanoic acid chloride (230 mg, 0.88 mm 3 ο 1) in THF (4mL) Stir vigorously at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate, washed with sodium bicarbonate solution and saturated brine 'and dried over magnesium sulfate. Concentrated by filtration 'and purified by silica gel chromatography. The title compound was obtained by dissolving in hexane-ethyl acetate (1: 1) (700 mg, yield 86%). 400 MHz 4 NMR (CDC13) δ 0.88 (12H, t, J 6.6 Hz), 1.25 (70H, bs), 1.40-1.80 (10H, m), 1.83-2.02 (4H, m), 2.17-2.22 (2H , M), 2.33 (1H, m), 3.10-3.36 (6H, m, including 3H, s, at 3.27 ppm), 3.38 (3H, s), 3.45-3.80 (1 2H, m), 3.81-4.10 ( 4H, m), 4.24-4.64 (8H, m), 5.2-5.4 (8H, m), 5.87-5.98 (3H, ni), 6.10 (1H, m) · (9) di; (¾propionate 4-O-dipropoxyfluorenyl-6-O- {2-deoxy-4-0-diallylphosphonic acid group 3 3 0-1 [(R) 3 3 methoxydecyl] 6- 〇—Methyl-2 — [(Z) —11— (octadecylpyridinyl) amino] —β—D—glucopyranosyl 丨 —3——O—dodecyl—2—0—ten Tetrayl-α-D-glucopyranoside (α-form) and diallylphosphonic acid group 4 -0 -allyloxycarbonyl group 6-0-{2 -deoxy-4-0-diallylphosphonic acid -3-O — [(R) —3-methoxydecyl] —O-methyl-1 — [(Z) —1 1— (octadecenyl) amino] —β—D — Pyranylglucosyl} -3-0-12 dodecyl-2-0-14 β — D — β Glucomannan 1 (β Bone Bean) (Ca 4th Project) 147-200413400 The compound (6 80 mg, 0.48 6 mmol) obtained in (8) was dissolved in dichloromethane (1 2 m L) '' Insert Na2S〇4 (1.5g), 1H-tetrazolium (142mg, 2 mm ο 1) and diisopropylamino diallyl phosphate (15.5 mg, 0.6 3 mm ο 1) under nitrogen Stir at room temperature for 30 minutes and purify by silica gel chromatography. Dissolve cyclohexane-ethyl acetate (1: 1) to obtain a quantitative oily phosphite. Dissolve the obtained phosphite in THF (25mL). Add 30% hydrogen peroxide water (500 mg, 4,4 1 mm ο 1), and stir for 30 minutes under ice cooling. Dilute the reaction solution with ethyl acetate, and add 10% thiosulfuric acid water and common salt. Washed with water, dried under magnesium sulfate, concentrated by filtration, and purified by silica gel chromatography. The solvent was dissolved in hexane-ethyl acetate (1: 1), and then dissolved in ethyl acetate to obtain the title compound as an oil (200 mg, yield 27%) and β-body (220mg, yield 30%). Alpha body: 400 MHz] H NMR (CDC13) δ 0 · 88 (12Η, t, J = 6.6 Ηζ), 1.26 (70H, bs), 1.40-1.73 (10H, m), 2.00-2.05 (4H, m) , 2.21- 2.25 (2H, m), 3.22-3.8 3 (22H, m, including two 3H, s, at 3.28 and 3.38 ppm), 3.96-4.02 (2H, m), 4.25 (1H? M), 4.54 -4.73 (11H, m), 5.23-5.40 (1 2H, m), 5.72 (1H, dd, J 2 3.3, 6.2 Hz), 5.89-5.99 (5H, m), 6.50 (1H, d, J = 8.1 Hz, NH). Β-body: 400 MHz 4 NMR (CDC13) δ 0 · 88 (12H, t, J = 6.6 Hz), ι · 26 (70H, bs), 1.40-1.75 (1 0H, m), 2.00 -2.02 (4H, m), 2.10-2.24 (2H, m), 3.1 8-3.80 (22H, m, including 2 3H, s, at 3.27 and 3 · 3 8 ρ pm), 4.00 (1 H , m), 4.2 5 (] H, m), 4 · 5 6-4.6 3 (1 1 H, m), 4.7 0 (1 H, d, J 2 8.8 H z), 4.9 5 (1 H, d ,;! 2 5.1, 8.1 Hz), 5. 1 3 200413400 (1H, d, J = 8.1 Hz), 5.23-5.43 (12H, m), 5.86-5.99 (5H, m), 7.50 (1H, d, J = 9.5 Hz, NH). (10) Phosphonic acid group 6—〇— {2 —Deoxy-3—〇 — [(R) — 3 —methoxydecyl] —6-0 — Methyl-2 — [(Z) —1 1- (octadecenyl) amino]-4-0-phosphonic acid-β-D-glucopyranosyl- 3-0-dodecyl- 2-0-tetradecyl-α — D —glucopyranoside (Project C a 5) Dissolve the α-form (200 mg, 0.055 mm) of the compound (9) in THF (15 mL), and add triphenylphosphine (35 mg, 0.13 mmol). Triethylamine (135 mg, 1.33 mmol), formic acid (120 mg, 2.6 mmol) and Pd (PPh3) 4 (35 mg, 0.0 3 mmol) were stirred under nitrogen at 5 5 ° C for 20 hours. The reaction solution was filtered, concentrated, and purified by a DEAE-cellulose 8 g column. After dissolving in a 0.05mol / L Ac0.NH4 solution of CHCl3-Me0H-H2O (2: 3: 1), a part containing the target substance can be obtained. Collect the mixture of the part and CHCl3-Me0H-H20 (1: 1: 1: 1), add CHC13 and 0.15mol / L hydrochloric acid water, stir in a separatory funnel, collect the lower layer of CHC13 and concentrate to obtain the standard standard Compound (100 mg, 57% yield). 400 MHz 4 NMR (CDC13-CD3〇D, 4: 1) δ 0.89 (12H, m), 1.27 (70H, bs), 1.40- 1.80 (1 0H, m), 2.01-2.03 (4H, m), 2.24 -2.26 (2H, m), 3.1 4- 3.92 (2 3 H, m, including 2 3H, s, at 3.30 and 3.40 ppm), 3.92-4.11 (2H, m), 4.72 (1H, d, J = 8.8 Hz), 5.34- 5.3 9 (2H, m), 5.63 (1H, m). FABMS (anion) m / z,] 3i2 [Μ-ΗΓ. C 6 6 Η 1 2 9 NO i 8 P 2値: c, 6 0.0 0; H, 10.2 3; N, 1.03; P, 200413400 4 · 5 5 ° Measured 値: C, 6 0.3 9; Η, 9.9 1; N, 1.28; P, 3.8 6. [Example 1 3] Phosphonic acidoxy) ethyl 6-〇- {2-deoxy-4-0-phosphonic acid group 3-0 ~ [(R) -3 3-methoxydecyl] —6— 0—methyl-1 — [(Z) —11 mono (octadecenyl) amino] -β-D-glucopyranosyl} -2,3-dione -Α-D-glucopyranoside (1) allyl 4,6--0-isopropylidene-a-D-glucopyranoside (Project A c 1) D-glucose (5g, 22.7 mmol) was dissolved in DMF (15mL), 2,2-dimethoxypropane (15mL) and p-Ts were added 0H (200 mg), and stirred at room temperature for 16 hours. The reaction solution was diluted with ethyl acetate, washed with sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated, and purified by silica gel chromatography. The title compound was obtained as an oil (3 g, yield 50%) by dissolving in cyclohexane-ethyl acetate (4: 1 to 2: 1). 400 MHz! H NMR (CDC13) δ 1.45 (3H, s), 1.52 (3H, s), 2.3 (1H, d, J = 10.3 Hz, OH), 2.79 (1H? D, 2.2 Hz, OH), 3.51 -3.88 (6H, m), 4.03 (1H, m), 4.23 (1H, m), 4.92 (1H, d, J = 3.7 Hz), 5.23-5.34 (2H, ni), 5.91 (1H, m ). (2) Allyl 2,3-di ~ 0-dodecyl-4,6--0-isopropylidene-α-D-glucopyranoside (Project ac 2) will be obtained by (1) The compound (5.4 g, 2 0.7 mm ο 1) and 1-iodine 12 (14,7 g, 49.6 mmol) were dissolved in DMF (3 mL), and sodium hydride (55% oil, 2, 4 g, 4 9.6 mm ο 1), and stirred at room temperature overnight. Methanol was added under ice-cooling to decompose sodium hydride. The reaction solution was diluted with ethyl acetate, washed with 150 200413400 water and saturated brine, and dried over magnesium sulfate. After filtration, it was concentrated and purified by silica gel chromatography. The title compound (7.4 g, yield 60%. 400 MHz) H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz) was obtained by dissolving in hexane-ethyl acetate (9: 1), 1.26 (36H, bs), 1.41 (3H, s), 148 (3H, s), 1.50-1.60 (4H, m), 3.49-3 · 73 (8H, m), 3.83 (1H, m), 4.08 ( 1H, dd, J = 6.6, 13.5 Hz), 4.18 (1H, dd, J = 5.1, 3.3 Hz), 4.9 (1H, d, J = 3.7 Hz), 5.22 (1H, m), 5.32 (1H, m ), 5.92 (1H, m). (3) 2-hydroxyethyl 2,3-di-0-dodecyl-4,6-6-isopropylidene-α-D-glucopyranoside (Abl project) The compound (4g, 6.7mol) obtained in (2) was dissolved in THF-H20 (7: 2, 66mL), and sodium periodate (6.7g) and 2.5% tungsten tetraoxide in the third butyl group were added. Alcohol (1.4mL) solution, stirred at room temperature for 2 hours, diluted with ethyl acetate. Washed with sodium bicarbonate solution and saturated brine, dried under magnesium sulfate. Filtered and concentrated to obtain the aldehyde residue. Dissolved in ethanol (50mL ), Add sodium borohydride (270mg), stir for 20 minutes, add acetic acid and dilute with ethyl acetate. Wash with sodium bicarbonate solution and saturated saline It was dried over magnesium sulfate. After filtration, it was concentrated and purified by silica gel chromatography. The title compound (4 4 8 mg, yield 41%) was obtained by dissolving in hexane-ethyl acetate (3: 1) as an oil. 400 MHz NMR (CDC13) δ 0.88 (9Η, t, J-6.6 Hz), 1.26 (36H, bs), 1.40 (3H, s), 1.41-1.43 (4H, m), ΐ · 48 (3H, s ), 2.82 (1H, bs, 0H), 3.30 (1H, m), 3.5 1-3.85 (i4H, m), 4.89 (1 H, d, J = 3. 7 H z) · -151-200413400 ( 4) 2 ~ (diallylphosphonic acidoxy) ethyl 2,3-di-12-dodecyl-4 '6-0-isopropylidene-α-D-glucopyranoside (p.ab 2 Engineering) The compound obtained in (3) (5.65 g, 9.2 mmol) was dissolved in dichloromethane (70 m L). The force [] was put into 1H — four-necked (1.54 g, 22 mmol), diisopropylamino phosphoric acid was fine Propionate (3.5 g, 1.3 mm) and sodium sulfate (6 g) were stirred at room temperature for 30 minutes. THF (70 mL) and 31% aqueous hydrogen peroxide (2 g) were added, and the mixture was stirred at room temperature for 15 minutes. The reaction solution was diluted with ethyl acetate, washed with a 10% Na 2 S 2 0 3 aqueous solution, a sodium bicarbonate solution, and saturated brine, and dried over magnesium sulfate. After filtration, it was concentrated and purified by silica gel chromatography. The title compound was obtained by dissolving cyclohexane-ethyl acetate (2: 1) (6.6 g, yield 99%). 400 MHz NMR (CDC13) δ 0.88 (6H, 1 = 6.6 Hz), 1.21-1.38 (36H, m), 1.39 (3H, s), 1.47 (3H, s), 1.5 0-1. 5 8 (4 H , m), 3.25-3.30 (1H, m), 3.51-3.88 (11H, m), 4.23-4.27 (2H, m), 4.56-4.60 (4H, m), 4.89 (1H, d, J. 2 · 3 · 7 Hz), 5.25-5.41 (4H, m), 5.91-6.00 (2H, m). (5) 2- (diallylphosphonic acidoxy) ethyl-2,3-di-O-dodecyl A-D-glucopyranoside (Project A b3) The compound (6.6 g, 9.1 mmol) obtained in (4) was dissolved in MeOH (60 mL), p-TsOH (4 12 mg) was added, and the mixture was stirred at room temperature for 2 After hours, it was concentrated and purified by silica gel chromatography. The title compound was obtained as a wax (6 g, yield 96%) by dissolving it in ethyl acetate and re-dissolving it in ethyl acetate solution containing j 0% MeOH. -] 52-200413400 400 MHz] H NMR (CDC13) δ 0.88 (6H, t, J-6.6 Hz), 1.26 (36H, bs), 1.5 0-1.71 (4H, m), 3.27 (1H, dd, J = 3.7, 8.8 Hz), 3.41-3.91 (11H, m), 4.24-4.28 (2H, m), 4.48-4.59 (4H, m), 4.95 (1H, d, J = 3.7 Hz), 5.19-5.40 ( 4H, m), 5.90-6 · 00 (2H, m). (6) 2- (di-dipropionyloxy) ethyl 6-0— {2—deoxy-4—〇—diene Propionate-3-O-[(R) -3-methoxydecyl] -6-O-methyl-2-[(2,2,2-dichloroethoxycarbonyl) amino] -β — D —glucopyranosyl} -2,3-dioxo-dodecyl —α — D -glucopyranoside (Project C b 1) Trichloromethylimidofluorenyl 2-deoxy One 4 one 0-diallylphosphonic acid group one 3-0 one [(R) three 3-methoxydecyl] one six-0 methyl one 2-[[2, 2, 2-trichloroethoxy (Carbonyl) amino] -α-D-glucopyranoside (lg, 1.18 mmol) (known compound, US Patent No. 5,9 3 5, 9 3 8) and (5) the compound obtained (1 · 0 2 g, 1.49 mm ο 1) dissolved in dichloromethane hospital (30mL) Sieve 4 A (1 .5mg), AgOTf (3 5 Omg, 1.36mmol) and TMS 〇Tf (20mg, 0.090mmol), under nitrogen and stirred overnight at room temperature embrace. The reaction solution was diluted with ethyl acetate, washed with a sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration, it was concentrated and purified by silica gel chromatography. The title compound was obtained by dissolving in ethyl acetate and then in an ethyl acetate solution containing 5% MeO (R), (lg, yield 60%). 400 MHz] H NMR (CDC13) δ 0.88 (9Η, t, 1 = 6.6 Hz), 1.26 (48H, bs), 1.3 8- 1.46 (2H, m), 1.5 3-1.5 8 (4H, η), 1.69 -1.77 (2 H: m), 2.6 (1 H, bs, 0H), 3 · 2 1-3. 8 9 (2 3 H, m, containing 2 3 H, s, -153-200413400 at 3 , 28 and 3.39 ppm), 4.09-4.3 2 (4H? M), 4.5 2-4.60 (8H, m)? 4-95 (1H? D, J = 3.7 Hz), 5.24-5.40 (8H, m), 5.89-5.99 (4H, 1T1), 6.41 (1H, wide, NH) · (?) 2- (diallylphosphonic acidoxy) ethyl 6—〇— {2—deoxy—4—〇—less Propionate — 3 — 0 — [(R) — 3 —methoxydecyl] — 6 — 0-methyl — 2 — [(z) — 11 (octadecenyl) amino] — β — D —glucopyranosyl — 2,3,210 —dodecyl a — D —pyranoside (Project C b 2) The compound obtained in (6) (500 mg, 0.35 mmol) It was dissolved in THF-acetic acid (3: 2, 15 mL), zinc powder (470 mg, 7.18 mmol) was added, and the mixture was stirred at room temperature for 4 hours. The reaction solution was filtered, concentrated, diluted with ethyl acetate ', washed with a sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration, the solution was concentrated, and the resulting primary amine was dissolved in THF (3 mL). A solution of sodium bicarbonate (124 mg) in water (0.9 mL) and cis-octadecenoic acid thallium chloride (200 mg, 0.72 mmol) in T H F (1.5 mL) were added and stirred vigorously at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate, washed with a sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration, it was concentrated and purified by silica gel chromatography. The title compound (400 mg, yield 75%) was obtained by dissolving in ethyl acetate and then dissolving in 5% MeOH in ethyl acetate. 400 MHz 'H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (66H, bs), 1.40- 1.7 9 (1 0H, ni), 1.99-2.04 (4H, m), 2.17_ 2.25 (2H, m), 3.0 1 (1H, bs, 0H), 3.17-3.8 2 (24H, m, containing 2 3 Η, s, at 3.28 and 3.38 pp ni), 3.97-4.31 ( 5 H, m), 4.5 2-4 · 5 8

200413400 (8H, m), 4.88 (1H, d, J-3.7 Hz), 5.13 (1H, d5 J-8.1 Hz), 5.23-5.38 ( 1 OH，m)，5.90-6.00 (4H，m)，6.62 (1H, d，J = 6.6 Hz, NH). (8) 2 —(膦酸氧基）乙基6—0— {2—去氧一 3 — O— [(R )—3 —甲氧癸基]—6— Ο —甲基一2—〔（Z) — 11—(十八碳烯醯基）胺基〕一 4 一 Ο -膦酸基一 β - D -吡喃葡糖基 }— 2，3 —二一 ◦一十二基一 α—D —吡喃葡糖苷（第Cb3 工程）將（7 )所得化合物（400mg，0.26 3 mmol )溶在無水THF (2 5 m L )，力□入二苯膦（35mg，0.133m mol)，三乙胺（ 140 mg，1 . 3 8 mmol )，甲酸（130mg，2.82mmol)及 Pd(PPh3)4 ( 3 5mg，0.2 2mmol )，於氮氣及 5 4 °C 攪拌 2 0 小時。將反應液過濾後濃縮，以DEAE-纖維素8 g之柱精製。溶離以 CHCl3-Me0H-H20 (2:3:1)之 0.05mol/L AcO'NHU 溶液可得含目的物之部份。收集部份與CHCl3-Me0H-H20 (1:1:1)之混合物，加入CHC13及0.15mol/L鹽酸水，於分液漏斗中攪拌，收集下層之CHC13層，濃縮，可得蠟狀之標邊化合物（160 mg，產率45%)。 IR vmax (KBr) 3 289 (br), 2924, 2853, 1 629 cm-1. 400 MHz 4 NMR (CDC13 + CD3〇D) δ 0.88 (12H，t，J = 6.6 Hz)，1.2 6 (6 6H，br s)，1.40- 1.7 9 ( 1 0H，m)，1.99-2.07 (4H， m), 2.17-2.25(2H，m), 3.20-3.90 (24H，m，含 2 個 3H, s，at 3.30 and 3.40 ppm), 4.00 —4.21 (5H，m)，4.65(1H，d, J = 8.1 Hz), 4.88 (1H, d? J-3.7 Hz), 5.3 7 - 5.40 (2H, m). -155 - 200413400 FABMS (陰離子）m/z，1 328 [Μ-ΗΓ. C68H133N〇19P2 分析計算値：C，59.7 6; Η，10.10; Ν，1.02; Ρ 4.53。實測値：C，5 9.4 9 ; Η，1 0 · 1 1 ; Ν，1 . 1 3 ; Ρ，4 · 0 2 · 〔實施例1 4〕 2—(膦酸氧基）乙基6 —〇一 {2 —去氧一3 —〇一[(R )一 3—甲氧癸基]—2— [(Z) — 11 —（十八碳烯醯基）胺基]一 4 一〇—膦酸基一 β — D —吡喃蔔糖基丨—2，3 —二一〇一十二基一 a — D —吡喃葡糖苷 (1)烯丙基2 —去氧一4，6 —〇一亞異丙基一3 —〇一[ (R) — 3—甲氧癸基]一 2—三氟乙醯胺基一 β— D —吡喃葡糖苷將烯丙基2 —去氧一 4，6-〇一亞異丙基一 2 —三氟乙醯胺基一β — D — 口比喃葡糖苷（Carb〇hydr，Res·，222， 57—68 ( 1991)，已知化合物）（17.8g，50.1mmol)溶在二甲基甲醯胺（250mL)，於0°C加入氫化鈉（4.05g，60% 油性，lOlmmol )，攪拌15分。加入對甲苯磺酸（R ) — 3 —甲氧癸酯（美國專利第5 9 3 5 9 3 8號，已知化合物）（ 18.9g，5 5.2mmol )，於室温下攪拌5小時。加入水以中止反應，以乙酸乙酯萃取3次，將有機層以水及飽和食鹽水依次洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，4 : 1 )，可得標題化合物（ 20.2g，產率 77%)。 IR vmax (KBr) 3 3 04，3 1 14，2 9 9 5，29 30，2 877, 2 85 8, 2 825, 1 7 0 5，1 674 cm-1 · 200413400 ]H-NMR ( 500 MHz，CDC13) δ 0.88 (3H，t，J = 6.8Hz)，1.27-1.47 (12H，m)，1.41 (3 H，s)，1.50 (3H，s), 1.63-1.67 (2H; m)，3.25 (1H，m)，3.28 (3H，s)，3.32 (1H，td，J = 9.8，4.9 Hz)，3.43 (1H，m)，3·58-3·64 (2H，m)，3.77- 3.8 7 (3 H，m)， 3.93 (1H，dd，J = 4.9，10.7 Hz), 4.06 (1H，dd, J-5.9, 12.7 Hz), 4.31 ( 1H, dd, J = 4.9，12.7 Hz), 4.88 (1H，d，J = 7.8 Hz), 5.19-5.28 (2H, m), 5.83 (1H，m)，6.56 (1H，d，J = 7.8 Hz， NH). MS (FAB,陽性）m/z，548 (M + Na) +，526 (M + H) + . HRMS (ESI，陽性），計算値 C25H42F3N07Na: 548.2808 ;實測値：5 4 8.2 8 1 5 . (2)烯丙基2 —去氧一 3—〇一[(R) — 3—甲氧癸基] 一 2—三氟乙醯胺基一 β - D —吡喃葡糖苷將（1)所得烯丙基2 —去氧一 4，6—〇一亞異丙基一 3 — 〇一[(R) — 3 —甲氧癸基]—2 —三氟乙醯胺基一β— D —吡喃葡糖苷（19.4g，36.9mmol)溶在甲醇（150mL)，加入對甲苯擴酸（3 8 9 m g，2 · 0 4 m m ο 1 )，於室温下攪拌2小時。將反應液減壓濃縮，以矽膠柱層析純化（己烷：乙酸乙酯，3 : 7 )，可得標題化合物（16.5g,產率92% )。 IR vmax (KBr) 3 548，3 375，3265, 3 1 1 6, 2927，2874，28 5 8， 1702，1 67 2 cm'1 · Α-ΝΜΙΐΗΟΟΜΗζ,ΟΟΟίηδΟ.δδρΗ,ί,^ό.όΗζ),：^?- 1 . 7 7 ( 1 4 Η， m)， 3 · 0 1 ( 2 Η，b r s，〇 Η )， 3.2 9 ( 3 Η， s)， 3 . 3 4 - 3 5 3 (3 Η，ηι)，3.5 9 ( ] Η，t，J = 9.5，8 . 8 Η ζ )，3.6 7 ( ] Η，m)，3.7 5 - 200413400 3.85 (3 H, m), 3.92 (1Η, dd, J-3.7, 11.7 Hz), 4.07 (1H, m), 4.31 (1H，m)，4·84 (1H，d，J = 8.8 Hz)，5.19-5.29 (2H，m). MS (FAB,陽性）m/z，508 (M + Na) +，4 8 6 (M + H) + . HRMS (ESI，陽性），計算値 C22H38F3N07Na·· 508.2494 ;實測値：5 0 8.2 5 0 3 . (3) (1—丙烯基）2—去氧一 3 —〇一[(R)— 3—甲氧癸基]—2—（2，2，2—三氯乙氧羰胺基）一β— D —吡喃葡糖苷將（2)所得烯丙基2 —去氧一 3 —〇—[(R) — 3—甲氧癸基]—2—三氟乙醯胺基一 β — D —吡喃葡糖苷（5.34g， 1 1,0mm〇l )溶在二甲亞颯（30mL )，加入第三丁氧化鉀（ 3.10g，27.6mmol )，於氮氣及85 °C下攪拌2小時。加入水（10mL)，於85°C下攬拌6小時，於室温下冷却，以二氯甲烷萃取3次。將有機層以水及飽和食鹽水依次洗浄，於硫酸鎂下乾燥，減壓蒸除溶劑，所得殘渣溶在四氫呋喃 (40mL)，加入飽和碳酸氫鈉水溶液（20mL)，氯甲酸2 ，2，2 —三氯乙酯（2.58 g，12.2 mmol )，於 0 °C 下攪拌 3 0 分。加入飽和碳酸氫鈉水溶液，以二氯甲烷萃取，將有機層以飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，2 : 3 )，可得標題化合物（4.70g,產率76% )。 IR vmax (KBr) 3 323, 3054, 2927, 2873, 2857, 1 7 1 6, 1 67 2, 1 6 4 2 cm'1 · 1 Η - N M R ( 5 0 0 Μ Η z 5 C D C 13 ) δ 0.8 9 ( 3 Η，t，J = 6.8 Η z )，1 . 2 8 - -158 - 200413400 1·62 (15H, m)，1·74- 1.79 (2H，m), 2.36 (1H，s，〇H)，3.3 0 (3H, s)，3.3 6 - 3.4 6 ( 3 H，m)，3.5 8-3.7 1 (3 H，m)，3.8 1 (1H， m), 3.90-3.94 (2H，m), 4.06 (1H，s，〇H)，4·57 1H，m)，4.74 (2H，s)，4.86 (1H，d，J = 6.8 Hz)，5.37 (1H，bi-s，NH)，6.15 (1H, m). MS (FAB,陽性）m/z，5 86 (M + Na) +，564 (M + H) + . HRMS (ESI，陽性），計算値 C23H40Cl3N〇8Na: 5 86.1 726 ; 實測値：586·1703. (4) (1 一丙烯基）6—〇一烯丙氧羰基一 2—去氧—3〜〇一[(R) — 3 —甲氧癸基]—2— (2，2，2 —三氯乙氧_ 胺基）一 β - D -吡喃葡糖苷將（3 )所得（1 —丙烯基）2 —去氧一 3 —〇—[(R )〜 3—甲氧癸基]一 2—（2，2，2—三氯乙氧羰胺基）一 —I]比喃葡糖苷（4 · 6 0 g，8 . 1 4 m m ο 1 )溶在二氯甲院（3 0 m L ) ，加入吡啶（1.4mL, 17.3 mmol )，氯甲酸烯丙酯（1 . 1 mL， 1 0.4 m m ο 1 )，於0 °C攪拌1小時。溶液中加入碳酸氫鈉水溶液，以二氯甲烷萃取3次，將有機層以水，飽和食鹽水依次洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，3 : 2 )，可得標題化合物（4.95g, 產率9 4 % )。 IR vmax (KBr) 3518，3 3 1 0, 3086，3 05 9，29 32，2 885，28 57， 1 7 2 8, 1 709，1 674, 1 65 2 cm'1 · 1 Η - N M R ( 5 0 0 Μ Η z，C D C 13 ) δ 0.8 9 ( 3 Η，t，J = 6.8 Η z )，1 , 2 5 -1·62 (15H, m)，1.7 0- 1.7 9 (2H. m)r 3.30 (3H, s), 3.36-3.44 -159 - 200413400 (2H，m)，3.50-3.71 (4H，m)，3.91-3.94 (2H，m，含〇 Η)，4·38 (1H，dd，J = 4.9，11.7 Hz)，4.50 (1H，dd，J 二2.0，11.7 Hz)， 4.56 (1H，m)，4.63 (2H，d，J二5.9 Hz)，4.74 (2H，s)，4,85 (1H，m)，5.2 6- 5.3 8 (3 H，m，含 NH)，5,93 (1H，m)，6.16 (1H， dd，J = 2.0，5.9 Hz). MS (FAB,陽性）m/z, 670 (M + Na) +，648 (M + H) + . HRMS (ESI，陽性），計算値 C27H44Cl3N01()Na: 670.1 9 14 ; 實測値·· 6 7 0.1 9 5 9 . (5) (1 —丙烯基）6—〇一烯丙氧羰基一 2—去氧—4 — 〇一二烯丙膦酸基一3 —〇一[(R) — 3—甲氧癸基]—2 — (2，2，2—三氯乙氧羰胺基）一 β— D —吡喃葡糖苷將（4)所得（1 一丙餘基）6—〇一條丙氧鐵基一 2-去氧一3 —〇一[(R) — 3 —甲氧癸基]—2— (2，2，2 —三氯乙氧羰胺基）—β — D —啦喃葡糖苷（4.80g，7.40mmol) 溶在四氫呋喃（30mL)，加入1 Η —四唑（830mg， 11.8 mmol)，雙（烯丙氧基）（二異丙胺基）膦（2.50g, l〇.2mmol )，於氮氣下，於室温下攪拌2小時。於0°C下冷却，加入30%過氧化氫水（10mL)，攪拌1小時，加入飽和硫代硫酸鈉水溶液，以乙酸乙酯萃取3次。將有機層以飽和碳酸氫鈉，飽和食鹽水依次洗浄，於硫酸鎂下乾燥，減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，3 : 2 )，可得標題化合物（5 . 1 7 g，產率8 6 % )。 IR vmax (CHC 1 3 ) 3 4 5 0，3 089，29 5 5, 2 87 3，2 8 5 9, 2 8 2 9，1 746, 1 6 7 4，1 6 5 0 cm-1 ·200413400 (8H, m), 4.88 (1H, d, J-3.7 Hz), 5.13 (1H, d5 J-8.1 Hz), 5.23-5.38 (1 OH, m), 5.90-6.00 (4H, m), 6.62 (1H, d, J = 6.6 Hz, NH). (8) 2 — (phosphonooxy) ethyl 6-0— {2—deoxy- 3 — O— [(R) —3 —methoxydecane Group] —6—O—methyl-1 — [(Z) — 11— (octadecenyl) amino] —4—10—phosphonic acid group—β-D-glucopyranosyl group— 2,3-Dione ◦ Dodecyl-α-D-glucopyranoside (Cb3 project) The compound (400 mg, 0.26 3 mmol) obtained in (7) was dissolved in anhydrous THF (2 5 m L). □ Add diphenylphosphine (35mg, 0.133m mol), triethylamine (140 mg, 1.38 mmol), formic acid (130mg, 2.82mmol) and Pd (PPh3) 4 (35mg, 0.22mmol) under nitrogen And stirred at 5 4 ° C for 20 hours. The reaction solution was filtered, concentrated, and purified by a DEAE-cellulose 8 g column. Dissolve the solution containing 0.05mol / L AcO'NHU in CHCl3-Me0H-H20 (2: 3: 1) to obtain the part containing the target substance. Collect the mixture of the part and CHCl3-Me0H-H20 (1: 1: 1), add CHC13 and 0.15mol / L hydrochloric acid water, stir in a separatory funnel, collect the lower CHC13 layer, and concentrate to obtain a waxy standard. Edge compound (160 mg, 45% yield). IR vmax (KBr) 3 289 (br), 2924, 2853, 1 629 cm-1. 400 MHz 4 NMR (CDC13 + CD3〇D) δ 0.88 (12H, t, J = 6.6 Hz), 1.2 6 (6 6H , Br s), 1.40-1.7 9 (1 0H, m), 1.99-2.07 (4H, m), 2.17-2.25 (2H, m), 3.20-3.90 (24H, m, including 2 3H, s, at 3.30 and 3.40 ppm), 4.00 —4.21 (5H, m), 4.65 (1H, d, J = 8.1 Hz), 4.88 (1H, d? J-3.7 Hz), 5.3 7-5.40 (2H, m) .- 155-200413400 FABMS (anion) m / z, 1 328 [M-ΗΓ. C68H133N019P2 Analytical calculation 値: C, 59.7 6; Η, 10.10; Ν, 1.02; P 4.53. Measured 値: C, 5 9.4 9; Η, 1 0 · 1 1; N, 1. 1 3; P, 4 · 0 2 · [Example 1 4] 2- (phosphonooxy) ethyl 6—〇 Mono {2-deoxy-3-0-[(R) -3-methoxydecyl] -2 — [(Z) — 11 — (octadecenyl) amino]] 4- 4-10-phosphine Acid group β-D-pyranoglycosyl--2,3-dioxoyl-12-yl-a-D-glucopyranoside (1) allyl 2-deoxy-4,6-- Monoisopropylidene-3-0-[(R) -3-methoxydecyl] -2-trifluoroacetamido-β-D-glucopyranoside allyl 2-deoxy-4 , 6-〇-isopropylidene-2-trifluoroacetamido-β-D-glucopyranoside (Carbohydr, Res., 222, 57-68 (1991), known compound) ( 17.8 g, 50.1 mmol) was dissolved in dimethylformamide (250 mL), and sodium hydride (4.05 g, 60% oily, 101 mmol) was added at 0 ° C, and stirred for 15 minutes. Add p-toluenesulfonic acid (R) -3-methoxydecyl ester (US Patent No. 5 9 3 5 9 38, known compound) (18.9 g, 5 5.2 mmol) and stir at room temperature for 5 hours. Water was added to stop the reaction, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane: ethyl acetate, 4: 1) to obtain the title compound (20.2 g, yield 77%). IR vmax (KBr) 3 3 04, 3 1 14, 2 9 9 5, 29 30, 2 877, 2 85 8, 2 825, 1 7 0 5, 1 674 cm-1 · 200413400] H-NMR (500 MHz , CDC13) δ 0.88 (3H, t, J = 6.8Hz), 1.27-1.47 (12H, m), 1.41 (3 H, s), 1.50 (3H, s), 1.63-1.67 (2H; m), 3.25 (1H, m), 3.28 (3H, s), 3.32 (1H, td, J = 9.8, 4.9 Hz), 3.43 (1H, m), 3.58-3 · 64 (2H, m), 3.77- 3.8 7 (3 H, m), 3.93 (1H, dd, J = 4.9, 10.7 Hz), 4.06 (1H, dd, J-5.9, 12.7 Hz), 4.31 (1H, dd, J = 4.9, 12.7 Hz), 4.88 (1H, d, J = 7.8 Hz), 5.19-5.28 (2H, m), 5.83 (1H, m), 6.56 (1H, d, J = 7.8 Hz, NH). MS (FAB, positive) m / z, 548 (M + Na) +, 526 (M + H) +. HRMS (ESI, positive), calculated 値 C25H42F3N07Na: 548.2808; found 値: 5 4 8.2 8 1 5. (2) Allyl 2 — to Oxy 3-0-[(R) — 3-methoxydecyl] 2-trifluoroacetamido-β-D-glucopyranoside (1) The obtained allyl 2-deoxy-4 , 6-O-isopropylidene-3-O-[(R) -3-methoxydecyl] -2-trifluoroacetamido-β-D-glucopyranoside (19 .4 g, 36.9 mmol) was dissolved in methanol (150 mL), p-toluene acid (389 mg, 2.0 m) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 3: 7) to obtain the title compound (16.5 g, yield 92%). IR vmax (KBr) 3 548, 3 375, 3265, 3 1 1 6, 2927, 2874, 28 5 8, 1702, 1 67 2 cm'1 · Α-ΝΜΙΐΗΟΟΜΗζ, 〇ΟΟίηδΟ.δδρΗ, ί, ^ ό.όΗζ) ,: ^?-1. 7 7 (1 4 Η, m), 3 · 0 1 (2 Η, brs, 0Η), 3.2 9 (3 Η, s), 3. 3 4-3 5 3 (3 Η, η), 3.5 9 (] Η, t, J = 9.5, 8.8 Η ζ), 3.6 7 (] Η, m), 3.7 5-200413400 3.85 (3 H, m), 3.92 (1Η, dd , J-3.7, 11.7 Hz), 4.07 (1H, m), 4.31 (1H, m), 4.84 (1H, d, J = 8.8 Hz), 5.19-5.29 (2H, m). MS (FAB, (Positive) m / z, 508 (M + Na) +, 4 8 6 (M + H) +. HRMS (ESI, positive), calculate 値 C22H38F3N07Na ·· 508.2494; found 値: 5 0 8.2 5 0 3. (3 ) (1-propenyl) 2-deoxy-3-0-[(R) -3-methoxydecyl] -2- (2,2,2-trichloroethoxycarbonylamino) -β-D -Pyranoglucoside will be obtained from (2) allyl 2-deoxy- 3-0-[(R)-3-methoxydecyl]-2-trifluoroacetamido-β-D-pyran Glucoside (5.34g, 1 1,0mm0l) was dissolved in dimethylarsin (30mL), and the third potassium butoxide was added 3.10g, 27.6mmol), stirred under nitrogen at 85 ° C 2 hours. Add water (10 mL), stir at 85 ° C for 6 hours, cool at room temperature, and extract 3 times with dichloromethane. The organic layer was washed with water and saturated brine in that order, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (40 mL), and a saturated aqueous sodium hydrogen carbonate solution (20 mL) was added. Chloroformic acid 2, 2, 2 —Trichloroethyl (2.58 g, 12.2 mmol), and stirred at 0 ° C for 30 minutes. A saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 2: 3) to obtain the title compound (4.70 g, yield 76%). IR vmax (KBr) 3 323, 3054, 2927, 2873, 2857, 1 7 1 6, 1 67 2, 1 6 4 2 cm'1 · 1 Η-NMR (50 0 Μ Η z 5 CDC 13) δ 0.8 9 (3 Η, t, J = 6.8 Η z), 1.2 8--158-200413400 1.62 (15H, m), 1.74- 1.79 (2H, m), 2.36 (1H, s, 〇 H), 3.3 0 (3H, s), 3.3 6-3.4 6 (3 H, m), 3.5 8-3.7 1 (3 H, m), 3.8 1 (1H, m), 3.90-3.94 (2H, m ), 4.06 (1H, s, 0H), 4.57 1H, m), 4.74 (2H, s), 4.86 (1H, d, J = 6.8 Hz), 5.37 (1H, bi-s, NH), 6.15 (1H, m). MS (FAB, positive) m / z, 5 86 (M + Na) +, 564 (M + H) +. HRMS (ESI, positive), calculate 値 C23H40Cl3N〇8Na: 5 86.1 726 Found): 586 · 1703. (4) (1 monopropenyl) 6-0-allyloxycarbonyl-2 deoxy-3 ~ 〇〇 [(R) — 3-methoxydecyl] -2— (2,2,2-Trichloroethoxy_amino) -β-D-glucopyranoside will be obtained from (3) (1-propenyl) 2-deoxy-3-0-[(R) ~ 3 —Methoxydecyl] —2- (2,2,2-trichloroethoxycarbonylamino) —I] pyranoside (4.60 g, 8.14 mm ο 1) is dissolved in two chlorine Hospital (3 0 m L), was added pyridine (1.4mL, 17.3 mmol), allyl chloroformate (1. 1 mL, 1 0.4 m m ο 1), stirred at 0 ° C 1 hour. An aqueous solution of sodium bicarbonate was added to the solution, and extraction was performed three times with dichloromethane. The organic layer was washed with water and saturated brine in that order, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 3: 2) to obtain the title compound (4.95 g, yield 94%). IR vmax (KBr) 3518, 3 3 1 0, 3086, 3 05 9, 29 32, 2 885, 28 57, 1 7 2 8, 1 709, 1 674, 1 65 2 cm'1 · 1 Η-NMR ( 5 0 0 Μ Η z, CDC 13) δ 0.8 9 (3 Η, t, J = 6.8 Η z), 1, 2 5 -1 · 62 (15H, m), 1.7 0- 1.7 9 (2H. M) r 3.30 (3H, s), 3.36-3.44 -159-200413400 (2H, m), 3.50-3.71 (4H, m), 3.91-3.94 (2H, m, inclusive), 4.38 (1H, dd , J = 4.9, 11.7 Hz), 4.50 (1H, dd, J 2.0, 11.7 Hz), 4.56 (1H, m), 4.63 (2H, d, J 5.9 Hz), 4.74 (2H, s), 4 , 85 (1H, m), 5.2 6- 5.3 8 (3 H, m, including NH), 5,93 (1H, m), 6.16 (1H, dd, J = 2.0, 5.9 Hz). MS (FAB, Positive) m / z, 670 (M + Na) +, 648 (M + H) +. HRMS (ESI, positive), calculate 値 C27H44Cl3N01 () Na: 670.1 9 14; measured 値 ·· 6 7 0.1 9 5 9 (5) (1-propenyl) 6-allyloxycarbonyl- 2 -deoxy-4--allylallylphosphonic acid -3 -〇-[(R)-3-methoxydecyl ] -2— (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside will be obtained from (4) (1-propionyl) 6-0 propoxy -2-deoxy-3-0-[(R) — 3-methoxydecyl] — 2 — (2,2,2-trichloroethoxycarbonylamino) —β — D —glucomannan (4.80g, 7.40mmol) was dissolved in tetrahydrofuran (30mL), and 1 Η -tetrazole (830mg, 11.8mmol), bis (allyloxy) (diisopropylamino) phosphine (2.50g, 10.2mmol) was added. Under nitrogen, stir at room temperature for 2 hours. After cooling at 0 ° C, 30% aqueous hydrogen peroxide (10 mL) was added, and the mixture was stirred for 1 hour. A saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted three times with ethyl acetate. The organic layer was washed successively with saturated sodium bicarbonate and saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate, 3: 2) to obtain the title compound. (5.17 g, 86% yield). IR vmax (CHC 1 3) 3 4 5 0, 3 089, 29 5 5, 2 87 3, 2 8 5 9, 2 8 2 9, 1 746, 1 6 7 4, 1 6 5 0 cm-1 ·

200413400 !H-NMR ( 500 MHz，CDC13) δ 0.88 (3H，t5 J = 6.8 Hz)，1.27、 1.56 (15H, m)，1.68-1.81 (2H，m)，3·29 (3H，s)，3.31 (1H， m)，3.47(lH，m)，3.72-3.82 (3H,m)，3.90(lH，m)，4.32-4.38 (2H, m), 4.52-4.63 (8H, m), 4.73 (2H, s), 4.99 (1H, m), 5.19-5.38 (6H? m), 5.56 (1H, m, NH), 5.89-5.99 (3H, m), 6· 13 (1H, m). MS (FAB,陽性）m/z，830 (M + Na) +，808 (M + H) + . HRMS (ESI，陽性），計算値 C33H53Cl3N〇13PNa: 830.22 1 5 ;實測値：8 3 0.2 2 3 1 . (6) 6—〇一烯丙氧類基一 2 —去氧一 4一〇一二録丙膦酸基一3 — ◦一 [(R) — 3 —甲氧癸基]—2— (2，2，2 — 三氯乙氧羰胺基）一 D -吡喃葡糖將（5 )所得（1 一丙烯基）6 —〇一烯丙氧羰基一 2 -去氧一 4 一〇一二烯丙膦酸基一 3 —〇一[(R) — 3 —甲氧癸基]一 2—（2，2，2—三氯乙氧擬胺基）一β - D — Π比喃葡糖苷（4.80g，5.9 3mmol )溶在四氫呋喃（30mL)，加入碘 (3.08g, 12.1mmol)，水（6mL )，於室温下攪拌 30 分。加入飽和硫代硫酸鈉水溶液，以乙酸乙酯萃取3次。將有機層以飽和碳酸氫鈉水溶液，飽和食鹽水依次洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，1 : 1 )，可得標題化合物（4.3 0 g ,產率9 4 % ) 〇 IR Vmax (CHC 1 3 ) 3 5 9 8，343 5，3317，3 089，2 95 5，293 1，2 8 7 3, 2 8 5 8，17 46, 1 6 5 1 cm"1 · -161 - 200413400 ]H-NMR ( 500 MHz，CDC13) δ 0.88 (3H，t，J = 6.8 Hz)， 1.26- 1.50 ( 1 2 H, m), 1.67-1.78 (2H, m): 3.26 (3H, s), 3.32 (1H，m)，3，63-3·73 (2H，m)，3.86-3.94 (2H，m), 4.18 (1H， m), 4.30-4.38 (3H, m), 4.51-4.63 (7H, m), 4.67, 4.74 (2H, AB-q, J = 11.7 Hz), 5.24-5.40 (7H, m), 5.81 (1H, d, J = 8.8 Hz, NH)，5.89-5,98 (3H，m). MS (FAB,陽性）m/z，790 (M + Na) +，7 6 8 (M + H) + . HRMS (ESI,陽性），I十算値 C3〇H5〇Cl3N〇i3P: 768.2085 ;實測値：7 6 8.2 0 8 9 . # (7)2—(二烯丙膦酸氧基）乙基 6 —〇一 {6 —〇一烯丙氧羰基一 2—去氧一4一〇一二烯丙膦酸基一3—〇一[( R) — 3 —甲氧癸基]一 2—（2，2，2 —三氯乙氧羰胺基） —β— D — B比喃葡糖基丨一2，3 —二一〇一十二基一a— D — 吡喃葡糖苷（第C b 1工程）將（6)所得6—〇一烯丙氧羰基一2 —去氧一 4 一 ◦一二烯丙膦酸基一3 —〇一[(R) — 3 —甲氧癸基]—2— (2，2200413400! H-NMR (500 MHz, CDC13) δ 0.88 (3H, t5 J = 6.8 Hz), 1.27, 1.56 (15H, m), 1.68-1.81 (2H, m), 3.29 (3H, s), 3.31 (1H, m), 3.47 (lH, m), 3.72-3.82 (3H, m), 3.90 (lH, m), 4.32-4.38 (2H, m), 4.52-4.63 (8H, m), 4.73 ( 2H, s), 4.99 (1H, m), 5.19-5.38 (6H? M), 5.56 (1H, m, NH), 5.89-5.99 (3H, m), 6.13 (1H, m). MS ( FAB, positive) m / z, 830 (M + Na) +, 808 (M + H) +. HRMS (ESI, positive), calculated 値 C33H53Cl3N〇13PNa: 830.22 1 5; found 値: 8 3 0.2 2 3 1 (6) 6-O-allyloxy- 2 -deoxy-4 10- 10-propionate- 3-◦-[(R)-3 -methoxydecyl]-2-( 2,2,2-Trichloroethoxycarbonylamino) -D-glucopyranose (5) will give (1-propenyl) 6-O-allyloxycarbonyl- 2-deoxy-4-10 Diallylphosphonic acid group 3—0 — [(R) — 3—methoxydecyl] —2— (2,2,2—trichloroethoxyamido) —β—D — π-glucopyranose Glycoside (4.80g, 5.93mmol) was dissolved in tetrahydrofuran (30mL), iodine (3.08g, 12.1mmol), water (6mL) was added, Temperature for 30 minutes. A saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution in this order, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane: ethyl acetate, 1: 1) to obtain the title compound (4.30 g, yield 94%). IR Vmax (CHC 1 3) 3 5 9 8,343 5,3317,3 089,2 95 5,293 1,2 8 7 3, 2 8 5 8,17 46, 1 6 5 1 cm " 1 · -161-200413400] H-NMR (500 MHz , CDC13) δ 0.88 (3H, t, J = 6.8 Hz), 1.26- 1.50 (1 2 H, m), 1.67-1.78 (2H, m): 3.26 (3H, s), 3.32 (1H, m), 3, 63-3 · 73 (2H, m), 3.86-3.94 (2H, m), 4.18 (1H, m), 4.30-4.38 (3H, m), 4.51-4.63 (7H, m), 4.67, 4.74 (2H, AB-q, J = 11.7 Hz), 5.24-5.40 (7H, m), 5.81 (1H, d, J = 8.8 Hz, NH), 5.89-5,98 (3H, m). MS (FAB , Positive) m / z, 790 (M + Na) +, 7 6 8 (M + H) +. HRMS (ESI, positive), I Calculate 値 C3〇H50Cl3N3i3P: 768.2085; Found 値: 7 6 8.2 0 8 9. # (7) 2- (diallylphosphonic acidoxy) ethyl 6-〇- {6--0-allyloxycarbonyl- 2-deoxy-4-10-diallyl Acid group 3—0 — [(R) —3-methoxydecyl] —2— (2,2,2-trichloroethoxycarbonylamino) —β—D — B glucopyranose丨 One 2,3-dioxoyl-12-a-D-glucopyranoside (Project C b 1) The 6-o-allyloxycarbonyl group 2- (6) -deoxy-4-1 ◦Diallylphosphonic acid group 3—〇 — [(R) — 3 —methoxydecyl] — 2 — (2, 2

，2 -三氯乙氧羰胺基）—D —吡喃葡糖（1 6 4 m g， I 0.2 13mmol )及實施例10 ( 5 )所得2 -（二烯丙膦酸氧基）乙基 2，3—二一〇一十二基一α — D —吡喃葡糖苷（ 1 17mg, 0. 162mmol )，依後述實施例1 6 ( 6 )之方法反應，可得標題化合物（125mg，產率52% )。 ]H-NMR ( 400 MHz, CDC13) δ 0.88 (9Η? t, J-6.6 Hz), 1 .26-1.44 ( 3 9 Η , m ), 1.5 3 - 1.60 ( 6 H ? m), 1.64- 1.7 9 ( 3 H , m), 2-50 (1 H，b r . s)，3 . 2 3 - 3 . 3 6 ( 8 H，m，含 3 H . s，a i 3.2 8 p p m )，3.4 5 - 200413400 3.92 (15H，m)，4.10 (1H，br.d，J 二 8.1 Hz), 4.19-4.36 (5H, m)，4.53-4.59 (10H，m)，4.63 (2H，d，J = 5.9 Hz), 4.68 (1H， br.d，J= 1 1 .7 Hz), 4.78 ( 1 H? d, J=ll.7 Hz)，4.88-4.91 (2H， m)，5.23-5.40 (10H，m), 5.88-5.98 (5H，m)，6.54 (1H，m). MS (FAB,陽性）m/z，1 492 (M + Na) + . (8) 2— （ —條丙鱗酸氧基）乙基 6 —〇一{6 —〇一稀丙氧類基一 2—去氧一 4一〇一一嫌丙膦酸基一 3—〇一[( R) — 3—甲氧癸基]一 2 - [(Z) —11 一（十八碳烯醯基 )胺基]一 β— D —吡喃葡糖基}一2，3—二一〇—十二基— α - D —吡喃葡糖苷（第C b 2工程）使用（7 )所得化合物（1 2 5 m g，0 · 0 8 4 9 m m ο 1 )，依後述實施例16 ( 7 )之方法反應，可得標題化合物（61. 8 mg，產率4 7 % )。 IR vmax (膜）3 300，3 085, 2925, 285 5，1 752, 1 65 2 cm-1 · 1H-NMR ( 500 MHz，CDC13 ) δ 0.8 8 (1 2 Η，t，J = 6 · 8 Η z)， 1.25 - 1.79 (77 H, m), 1.99-2.01 (3H, m), 2.16-2.24 (2H, m), 2.87 (1H, d, J = 3.9 Hz), 3.12-3.17 (1H, m), 3.24 ( 1H, dd, J:9.8，2.9 Hz)，3.26-3.38 (5H，m，含 3H，s，at 3.28 ppm)， 3.45-3.55 (3H，m)，3.57-3.85 (8H，m)，4.02-4.06 (1H，m)， 4.10 (1H, d，J=10.7 Hz), 4.16-4.33 (3H, m), 4.51-4.64 (1 2H, m), 4.88 (1H，d, J:3.9 Hz), 5.19 (1H，d，J = 7.8 Hz), 5.23-5.40 (12H，m)，5.89-5.98 (5H，m)，6.74 (1H，d，J = 6.8 Hz). MS (FAB,陽性）m / z，1— 4 2 2 ( M + N a ) ' 1 4 0 0 ( M + H ) 200413400 HRMS (FAB，陽性），計算値 C83H151021NP2Na: 158.0161 ; 實測値：1 5 8 3.0 1 7 9 . (9) 2— （膦酸氧基）乙基 6 —〇一{2—去氧一3—〇 —[(R) — 3 —甲氧癸基]一 2— [(Z) — 11—(十八碳烯醯基）胺基]一 4 一〇一膦酸基一 β — D —吡喃葡糖基} 一 2， 3—二一〇一十二基一α-D —吡喃葡糖苷（第Cb3工程 ) 使用（8 )所得化合物（1 3 6 m g , 0.0 8 7 1 m m ο 1 )，依後述實施例16 ( 8 )之方法反應，可得標題化合物（87.2mg，產率7 6 % )。 IR vmax (KBr) 3 285, 3064，3005，2955，2923，285 3，2327， 1716，1 657，1 632 cm"1 · ]H-NMR ( 500 MHz, CD3〇D + CDCl3) δ 0.90 (12H, t, J = 6.8 Hz), 1.29- 1.46 (70H, m), 1.5 6- 1.74 (8H, m), 2.01-2.04 (4H, m)5 2.24-2.2 8 (2H? m), 3.20 (1H, dd, J = 3.9? 9.8 Hz), 3.30 (3H, s), 3.31-3.40 (2H, m), 3.45-3.49 (2H, m), 3.53-3.56 (1H, m), 3.62-3.88 (12H, m), 4.07-4.17 (4H, m), 4.49 (1H, d, J = 8.8 Hz), 4.92 (1H, d, 1 = 3.9 Hz), 5.3 3 -5.3 5 (2H, m). MS (ESI，陰性）m/z, 1314 (M-H)-. HRMS (ESI，陰性），計算値 C67Hi30N〇19P2: 1 3 1 4.8708 ;實測値：1 3 1 4.8 6 9 4 . 〔實施例1 5〕 2—膦酸氧乙基 6 —〇一 {2 —去氧一3 — ◦一 [(R) — 3 一羥癸基]一 2—[(Z) — 11—十八碳烯醯胺基]一 4 —〇一 164 - 200413400 膦酸基一 β— D —吡喃葡糖基丨一 2，3—二—〇一十二基—α 一 D -吡喃葡糖苷 (1) 2— (4 —甲氧苯基）一（R) — 4 —庚基一 [1，3] 二曙烷將（R ) — 3 —羥基一1 —癸醇（美國專利第5 9 3 5 9 3 8號，已知化合物）（17.4g，99.8mmol )溶在甲苯（250mL ) ，加入對一茴香醛二甲縮醛（2 0.0 g，1 1 0 m m ο 1 )及對甲苯磺酸（1.8 Og, 9.4 6 mmol )，於室温下攪拌2小時。將反應液減壓濃縮，以乙酸乙酯稀釋，以水，飽和碳酸氫鈉水溶液及飽和食鹽水依次洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，9 : 1 )，可得標題化合物（25.8g，產率88% )。 IR vmax (CHC13) 345 0，2927，28 5 5, 1 74 8，1 650 cm'1 · 'H-NMR ( 500 MHz, CDC13 ) δ : 0.88 (3H，t, J = 6.8 Hz)， 1.27-1.54 (12H，m)，1.64-1.82 (2H, m)，3.76-3.84 (4H，m,含 3H, s, at 3.80 ppm), 3.93 (1H, td, J-2.0, 11.7 Hz), 4.24 (lH，dd，J = 4.9，11.7Hz)，5.46(lH，s)，6.88(2H，d，J = 8.8 Hz)，7.42(2H，d，J = 8.8Hz). MS (El,陽性）m/z，292 (M + ·). HRMS (EI，陽性），計算値 CISH28〇3: 29 2.202 8 ;實測値： 292.2043. (2) (R)— 3 — （4 一甲氧苄氧基）一 1 一癸醇將（1 )所得2 — （ 4 一甲氧苯基）一（R ) 一 4 —庚基一 [1，3 ]二噚烷（2 5.6 g，8 7 . 5 m m ο 1 )溶在甲苯（2 0 0 m L )，於 165 200413400 ◦°C下加入1.0mol/L氫化二異丁銨/甲苯溶液（135mL, 135mmol )，於室温下攬拌5小時。將反應液於0 °C下冷却，緩慢地加入飽和氯化錢水溶液以中止反應，加入 0.5 mol/L Rochelle鹽水溶液，於室温下攪拌30分。以乙酸乙酯萃取3次，將有機層以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，7 : 3 )，可得標題化合物（23.8g，產率92% )。 IR vmax (CHC13 ) 3 6 2 5, 3 500，295 6，293 1，2 8 5 8，1613 cm'1 · ^-NMR ( 400 MHz, CDC13) δ : 0.8 9 ( 3 Η，t，J 二 6 · 6 Η z)， 1.28- 1.3 5 ( 1 0Η, m)，1.48 - 1.8 5 (4H, m)，2.46 (1H，t，J = 5.8 Hz，〇H)，3.62 (1H，m)，3.68-3.83 (5H，m，含 3H，s，at 3.80 ppm), 4.41, 4.53 (2H，A B - q，J = 1 1 · 0 H z )，6.8 6 - 6.9 0 ( 2 H，m)， 7.24-7.28 (2H, m). MS (FAB,陽性）m/z, 3 17 (M + Na) + , 295 (M + H) + . HRMS (ESI，陽性），計算値 C18H3〇03Na·· 3 1 7.2098 ;實測値：317.2090. (3)甲磺酸（R) — 3—（4 一甲氧苄氧基）癸酯將（2)所得（R) — 3—（4 一甲氧苄氧基）一 1 一癸醇 (23.5g, 79.8 mmol)溶在二氯甲烷（3 0 0 m L )，於 0 °C 下加入三乙胺（1 6 · 7 m L , 1 2 0 m m ο 1 )及甲擴醯氯（7.4 m L, 96mmol )，攪拌1小時。反應液中加入飽和碳酸氫鈉水溶液，以二氯甲烷萃取，將有機層以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，7 : 3 )，可得標題化合物（27.8g,產率 -]66 - 94% )。 94% )。200413400 IR vmax (CHC13) 29 57，29 3 1，28 5 8，1613 cm-1 . 】H-NMR ( 400 MHz，CDC13 ) δ 0 · 8 9 ( 3 H，t，J 二 6.9 H z )， 1.24-1.37 (10H，m)，1.47-1.66 (2H，m)，1.83-1.99 (2H，m)， 2.95 (3H，s)，3.55 (1H，m)，3·80 (3H，s)，4.27-4.3 6 (2H，m), 4.38, 4.51 (2H, AB-q, J^ll.O Hz), 6.86-6.90 (2H, m), 7.24-7.28 (2H? m). MS (FAB，陽性）m/z，395 (M + Na) + . HRMS (ESI，陽性），計算値 C19H32〇5SNa: 3 9 5.1 8 5 2 ;實測 _ 値：395.1878. (4)烯丙基2 —去氧一4’ 6—〇一亞異丙基一 3 —〇一[ (R) — 3—（4 一甲氧苄氧基）癸基]一 2—三氟乙醯胺基一 α — D -吡喃葡糖苷將烯丙基2 —去氧一 4，6—〇—亞異丙基一 2—三氟乙醯胺基一a — D — 口比喃匍糖甘（Carbohydr-Res·，222， 57—68 ( 1991)，已知化合物）（17.2g，48.4mmol)溶在二甲基甲醯胺（150mL)，於0°C下加入氫化鈉（3.88g， _ 60 %油性，97 mmol )並攪拌15分。加入（3 )所得甲磺酸（ R) — 3— (4 —甲氣卞氧基）癸醋（15.lg，40.5 mmol)，於室温下攪拌5小時。加入水以中止反應，以乙酸乙酯萃取3次，將有機層以水及飽和食鹽水依次洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，4 : 1 )，可得標題化合物（2 1 · 3 g :產率8 3 % )。 IR vmax (CHC 1 3 ) 3 4 3 0，2 9 3 1，2 8 5 9，17 3 4，1612 cm_i · -167 - 200413400 ]H-NMR ( 400 MHz, CDC13) δ 0.88 (3H，t，J二6.6 Hz)， 1.24- 1.5 2 ( 1 8 H , m，含 3 H，s，at 1.40 p p m ; 3 H , s , at 1.49 ppm)，1.64-1.76 (2H，m)5 3.42-3.49 (2H，m); 3.58 (1H，m)， 3.66-3.78 (3H, m)，3.80 (3H，s)，3.84-3.89 (2H，m)，3.99 (1H, dd，J = 6.6，12.5 Hz), 4.14-4.20 (2H，m)，4.36，4.42 (2H, AB-q，J=ll.7 Hz)，4.87 (1H, d, J 二 3·7 Hz)，5.24-5.30 (2H，m), 5.86 (1H，m)，6.42 (1H，d，J = 9.5Hz，NH)，6.85-6.89 (2H, m)? 7.23 -7.27 (m, 2H). MS (FAB,陽性）m/z，654 (M + Na) +，632 (M + H) + . _ HRMS (ESI，陽性），計算値 C32H48F3N08Na: 654.3 229 ;實測値：6 5 4.3 2 3 2 . (5)烯丙基2 —去氧一 3—〇一 [(R) — 3—（4 —甲氧苄氧基）癸基]一 2-三氟乙醯胺基一 α-D —吡喃葡糖苷將（4)所得烯丙基2—去氧一 4，6—〇一亞異丙基一 3 —〇一[(R) —3—（4 一甲氧苄氧基）癸基]一 2—三氟乙醯胺基一 a — D —吡喃葡糖苷（21.0g，33.2mmol)，依實施例14 ( 2 )之方法反應，可得標題化合物（17.9g，產率 $ 9 1%)。 IR vmax (KBr) 3425，3315，3095, 2961，2928，2858，1699， 1666，1 647 cm'1 · !H-NMR ( 400 MHz, CDC13) δ 0.88 (3H，t, J二6·6 Hz)， 1.26- 1.8 2 ( 1 4H，m), 2,32 (2H，brs，〇H)，3.47-3.5 8 (3 H，m)， 3.6 4 - 3.7 0 ( 2 H , m)，3.7 3 - 3.7 9 ( 3 H，m)，3 . 8 1 ( 3 H，s)，4.0 0 (1 H , m )，4 . 1 2 - 4.2 ] ( 2 ] ί，m )，4 · 3 8，4 · 4 3 ( 2 H，A B - q，J 二 1 1 . 7 -168- 200413400, 2-trichloroethoxycarbonylamino) -D-glucopyranose (164 mg, I 0.2 13 mmol) and 2- (diallylphosphonic acidoxy) ethyl 2 obtained in Example 10 (5) , 3-21012-α-D-glucopyranoside (117 mg, 0.162 mmol) was reacted according to the method of Example 16 (6) described later to obtain the title compound (125 mg, yield 52%). ] H-NMR (400 MHz, CDC13) δ 0.88 (9Η? T, J-6.6 Hz), 1.26-1.44 (3 9 Η, m), 1.5 3-1.60 (6 H? M), 1.64- 1.7 9 (3 H, m), 2-50 (1 H, br. S), 3. 2 3-3. 3 6 (8 H, m, with 3 H. S, ai 3.2 8 ppm), 3.4 5- 200413400 3.92 (15H, m), 4.10 (1H, br.d, J 8.1 Hz), 4.19-4.36 (5H, m), 4.53-4.59 (10H, m), 4.63 (2H, d, J = 5.9 Hz ), 4.68 (1H, br.d, J = 1 1 .7 Hz), 4.78 (1 H? D, J = 11.7 Hz), 4.88-4.91 (2H, m), 5.23-5.40 (10H, m ), 5.88-5.98 (5H, m), 6.54 (1H, m). MS (FAB, positive) m / z, 1 492 (M + Na) +. (8) 2— (—Protonic acid) ) Ethyl 6-〇- {6-0-dilute propoxy group- 2 -deoxy-4 10- 1-propylphosphonic acid group 3-0-[(R)-3-methoxydecyl] -2-[(Z) —11 mono (octadecenyl) amino] -β-D -glucopyranosyl} -2,3-dioxo-dodecyl-α-D-pyridine Glucosinolate (Project C b 2) Using the compound (7) obtained in (7) (125 mg, 0 · 0 8 4 9 mm ο 1), the reaction was carried out according to the method of Example 16 (7) described later, and the title was obtained. Compound (61.8 mg, 47.7% yield). IR vmax (film) 3 300, 3 085, 2925, 285 5, 1 752, 1 65 2 cm-1 · 1H-NMR (500 MHz, CDC13) δ 0.8 8 (1 2 Η, t, J = 6 · 8 Η z), 1.25-1.79 (77 H, m), 1.99-2.01 (3H, m), 2.16-2.24 (2H, m), 2.87 (1H, d, J = 3.9 Hz), 3.12-3.17 (1H, m), 3.24 (1H, dd, J: 9.8, 2.9 Hz), 3.26-3.38 (5H, m, including 3H, s, at 3.28 ppm), 3.45-3.55 (3H, m), 3.57-3.85 (8H, m), 4.02-4.06 (1H, m), 4.10 (1H, d, J = 10.7 Hz), 4.16-4.33 (3H, m), 4.51-4.64 (1 2H, m), 4.88 (1H, d, J : 3.9 Hz), 5.19 (1H, d, J = 7.8 Hz), 5.23-5.40 (12H, m), 5.89-5.98 (5H, m), 6.74 (1H, d, J = 6.8 Hz). MS (FAB , Positive) m / z, 1— 4 2 2 (M + Na) '1 4 0 0 (M + H) 200413400 HRMS (FAB, positive), calculate 値 C83H151021NP2Na: 158.0161; found;: 1 5 8 3.0 1 7 9. (9) 2- (phosphonooxy) ethyl 6-0- {2-deoxy-3-0-[(R) — 3 -methoxydecyl] -2 — [(Z) — 11- (octadecenyl) amino] -4,10-phosphonic acid-β-D-glucopyranosyl} -2,3-dioxalyl-12-yl-α-D — Pyranoside (Project Cb3) Using the compound (8) obtained in (8) (136 mg, 0.0 8 7 1 mm ο 1), the reaction was performed according to the method of Example 16 (8) described later to obtain the title compound (87.2 mg, Yield 76.6%). IR vmax (KBr) 3 285, 3064, 3005, 2955, 2923, 285 3, 2327, 1716, 1 657, 1 632 cm " 1 ·] H-NMR (500 MHz, CD3〇D + CDCl3) δ 0.90 (12H , t, J = 6.8 Hz), 1.29- 1.46 (70H, m), 1.5 6- 1.74 (8H, m), 2.01-2.04 (4H, m) 5 2.24-2.2 8 (2H? m), 3.20 (1H , dd, J = 3.9? 9.8 Hz), 3.30 (3H, s), 3.31-3.40 (2H, m), 3.45-3.49 (2H, m), 3.53-3.56 (1H, m), 3.62-3.88 (12H , m), 4.07-4.17 (4H, m), 4.49 (1H, d, J = 8.8 Hz), 4.92 (1H, d, 1 = 3.9 Hz), 5.3 3 -5.3 5 (2H, m) .MS ( ESI, negative) m / z, 1314 (MH)-. HRMS (ESI, negative), calculate 値 C67Hi30N019P2: 1 3 1 4.8708; measured 値: 1 3 1 4.8 6 9 4. [Example 1 5] 2 —Phosphonooxyethyl 6 —0— {2 —deoxy—3 — ◦-[(R) — 3 -hydroxydecyl] —2 — [(Z) — 11-octadecenylamino] — 4—〇一 164-200413400 Phosphonate-β-D-glucopyranosyl 丨 -2,3-di-12-dodecyl-α-D-glucopyranoside (1) 2— (4 — (Methoxyphenyl)-(R) — 4 —heptyl- [1,3] dioxane will (R) — 3 —hydroxy-1 —decanol (US Patent No. 5 9 3 5 9 3 8, known compound (17.4 g, 99.8 mmol) was dissolved in toluene (250 mL), and p-anisaldehyde dimethyl acetal (2 0.0 g, 1 10 mm ο 1) was added And p-toluenesulfonic acid (1.8 Og, 9.4 6 mmol), and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with water, a saturated sodium bicarbonate aqueous solution and saturated brine in this order, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 9: 1) to obtain the title compound (25.8 g, yield 88%). IR vmax (CHC13) 345 0, 2927, 28 5 5, 1 74 8, 1 650 cm'1 · 'H-NMR (500 MHz, CDC13) δ: 0.88 (3H, t, J = 6.8 Hz), 1.27- 1.54 (12H, m), 1.64-1.82 (2H, m), 3.76-3.84 (4H, m, including 3H, s, at 3.80 ppm), 3.93 (1H, td, J-2.0, 11.7 Hz), 4.24 ( lH, dd, J = 4.9, 11.7 Hz), 5.46 (lH, s), 6.88 (2H, d, J = 8.8 Hz), 7.42 (2H, d, J = 8.8 Hz). MS (El, positive) m / z, 292 (M + ·). HRMS (EI, positive), calculated 値 CISH28〇3: 29 2.202 8; found 値: 292.2043. (2) (R) — 3 — (4 monomethoxybenzyloxy) 1 1-decyl alcohol will give 2- (4-monomethoxyphenyl)-(R) -4-heptyl- [1,3] dioxane (2 5.6 g, 8 7. 5 mm) obtained from (1) ) Dissolved in toluene (200 m L), added 1.0 mol / L diisobutylammonium hydrogen / toluene solution (135mL, 135mmol) at 165 200413400 ◦ ° C, and stirred at room temperature for 5 hours. The reaction solution was cooled at 0 ° C, and a saturated aqueous solution of hydrochloric acid was slowly added to stop the reaction. A 0.5 mol / L Rochelle saline solution was added, and stirred at room temperature for 30 minutes. It was extracted three times with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 7: 3) to obtain the title compound (23.8 g, yield 92%). IR vmax (CHC13) 3 6 2 5, 3 500, 295 6, 293 1, 2 8 5 8, 1613 cm'1 · ^ -NMR (400 MHz, CDC13) δ: 0.8 9 (3 Η, t, J 2 6 · 6 Η z), 1.28- 1.3 5 (1 0Η, m), 1.48-1.8 5 (4H, m), 2.46 (1H, t, J = 5.8 Hz, 0H), 3.62 (1H, m), 3.68-3.83 (5H, m, including 3H, s, at 3.80 ppm), 4.41, 4.53 (2H, AB-q, J = 1 1 · 0 H z), 6.8 6-6.9 0 (2 H, m), 7.24-7.28 (2H, m). MS (FAB, positive) m / z, 3 17 (M + Na) +, 295 (M + H) +. HRMS (ESI, positive), calculate 値 C18H3〇03Na ·· 3 1 7.2098; Measured tritium: 317.2090. (3) (R) — 3- (4-monomethoxybenzyloxy) decyl The (R) — 3- (4 monomethoxybenzyloxy) obtained from (2) Group)-1-decanol (23.5g, 79.8 mmol) was dissolved in dichloromethane (300 m L), and triethylamine (16 · 7 m L, 1 2 0 mm) was added at 0 ° C. ) And methyl chloride (7.4 ml, 96 mmol), and stirred for 1 hour. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 7: 3) to obtain the title compound (27.8 g, yield-] 66-94%). 94%). 200413400 IR vmax (CHC13) 29 57, 29 3 1, 28 5 8, 1613 cm-1.】 H-NMR (400 MHz, CDC13) δ 0 · 8 9 (3 H, t, J 2 6.9 H z), 1.24-1.37 (10H, m), 1.47-1.66 (2H, m), 1.83-1.99 (2H, m), 2.95 (3H, s), 3.55 (1H, m), 3.80 (3H, s), 4.27-4.3 6 (2H, m), 4.38, 4.51 (2H, AB-q, J ^ ll.O Hz), 6.86-6.90 (2H, m), 7.24-7.28 (2H? M). MS (FAB, (Positive) m / z, 395 (M + Na) +. HRMS (ESI, positive), calculated 値 C19H32〇5SNa: 3 9 5.1 8 5 2; found _ 値: 395.1878. (4) allyl 2 —deoxy -4 '6-0-isopropylidene-3-0-[(R)-3-(4-methoxymethoxybenzyloxy) decyl]-2-trifluoroacetamido-α-D-pyridine Glucosinolates allyl 2-deoxy-4,6--0-isopropylidene-2 2-trifluoroacetamido-a-D-glucopyranoside (Carbohydr-Res ·, 222, 57-68 (1991), a known compound) (17.2 g, 48.4 mmol) dissolved in dimethylformamide (150 mL), and sodium hydride (3.88 g, -60% oily, 97 mmol) was added at 0 ° C. And stir for 15 minutes. Add (3) the obtained methanesulfonic acid (R) —3- (4-methylaminofluorenyloxy) decanoate (15.lg, 40.5 mmol), and stir at room temperature for 5 hours. Water was added to stop the reaction, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, 4: 1) to obtain the title compound (21.3 g: yield 83%). IR vmax (CHC 1 3) 3 4 3 0, 2 9 3 1, 2 8 5 9, 17 3 4, 1612 cm_i · -167-200413400] H-NMR (400 MHz, CDC13) δ 0.88 (3H, t, J 2 6.6 Hz), 1.24- 1.5 2 (18 H, m, including 3 H, s, at 1.40 ppm; 3 H, s, at 1.49 ppm), 1.64-1.76 (2H, m) 5 3.42-3.49 ( 2H, m); 3.58 (1H, m), 3.66-3.78 (3H, m), 3.80 (3H, s), 3.84-3.89 (2H, m), 3.99 (1H, dd, J = 6.6, 12.5 Hz) , 4.14-4.20 (2H, m), 4.36, 4.42 (2H, AB-q, J = ll.7 Hz), 4.87 (1H, d, J = 3.7 Hz), 5.24-5.30 (2H, m) , 5.86 (1H, m), 6.42 (1H, d, J = 9.5Hz, NH), 6.85-6.89 (2H, m)? 7.23 -7.27 (m, 2H). MS (FAB, positive) m / z, 654 (M + Na) +, 632 (M + H) +. _ HRMS (ESI, positive), calculate 値 C32H48F3N08Na: 654.3 229; found 値: 6 5 4.3 2 3 2. (5) allyl 2 — to Oxy 3-0-[(R) — 3- (4-methoxybenzyloxy) decyl] 2-trifluoroacetamido-α-D-glucopyranoside 2-Deoxy-4,6-0-isopropylidene-3-0-[(R) —3- (4-methoxymethoxybenzyloxy) decyl] 2-trifluoroacetamidine Amino-a-D-glucopyranoside (21.0 g, 33.2 mmol) was reacted in the same manner as in Example 14 (2) to obtain the title compound (17.9 g, yield 91.1%). IR vmax (KBr) 3425, 3315, 3095, 2961, 2928, 2858, 1699, 1666, 1 647 cm'1 ·! H-NMR (400 MHz, CDC13) δ 0.88 (3H, t, J = 6.6 Hz ), 1.26- 1.8 2 (1 4H, m), 2,32 (2H, brs, 0H), 3.47-3.5 8 (3 H, m), 3.6 4-3.7 0 (2 H, m), 3.7 3 -3.7 9 (3 H, m), 3. 8 1 (3 H, s), 4. 0 (1 H, m), 4. 1 2-4.2] (2] ί, m), 4 · 3 8, 4 · 4 3 (2 H, AB-q, J 2 1 1. 7 -168- 200413400

Hz)，4.85 (1H，d, J 二 3·7 Hz)，5.24-5.31 (2H，m)5 5·87 (1Η， m)，6.4 2 ( 1 Η，d，J 二 9.5 Η z )，6 · 8 6 - 6.9 0 ( 2 Η , m )，7.2 5 (2 Η，d , J 二 8.8 Hz). MS (FAB，陽性）m/z，614 (M + Na) +，5 92 (M + H) + . HRMS (ESI,陽性），計算値 C29H44F3N08Na: 6 1 4.290 1 ;實測値：6 1 4.2 9 4 3 . (6)條丙基2 —去氧一 3 —〇一 [(R) — 3— (4 —甲氧苄氧基）癸基]一 2—（2，2，2—三氯乙氧羰胺基）一 α-D -吡喃葡糖苷將（5)所得燒丙基2 —去氧一 3 —〇一 [(R) — 3—（4 一甲氧苄氧基）癸基]一 2—三氟乙醯胺基一 α— D —吡喃葡糖苷（5.6 1g，9.48mmol )溶在乙醇（40mL )，加入 lmol/L 氫氧化鈉水溶液（40mL)，於8CTC攪拌5小時。將反應液減壓濃縮，以乙酸乙酯稀釋，以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，所得粗胺溶在四氫呋喃（ 25mL)，於下加入飽和碳酸氫鈉水溶液（25mL)及氯甲酸2，2，2 —三氯乙酯（2.20g，10.4mm 〇1)，攪拌30分。反應液中加入飽和碳酸氫鈉水溶液，以乙酸乙酯萃取3 次，將有機層以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，2 : 3 )，可得標題化合物（6 · 0 1 g，產率9 5 % )。 IR vmax (KBr) 3 3 49，3 065，295 5, 2927, 2 85 6, 1 7 1 3, 1 646, 16 14 cm"1 · 1 Η - Ν Μ R ( 4 0 0 MHz, C D C J 3 ) δ 0.8 8 ( 3 H，t，J 二 6.6 H z )， 200413400 1.26- 1.80 (14 Η，m)，2.04 ( 1 Η, t，OH), 3.42-3.90 ( 1 3 H, m，含 3H，s，at 3.80 ppm)，3.99 (1H, dd，J = 6.6，12.4 Hz), 4.19 (1H，m)，4.39，4.44 (2H, AB-q，J=11.0 Hz)，4.69，4.74 (2H， AB-q, J-12.1 Hz), 4.85 (1H, d, J-3.7 Hz), 5.19-5.32 (3H, m，含 NH)，5.84-5.94 (1H，m)，6.86-6.89 (2H, m)，7.24-7.27 (2H，m). MS (FAB,陽性）m/z，692 (M + Na) + . HRMS (ESI,陽性），計算値 C30H46Cl3NO9Na: 692.2141 ; 實測値：6 9 2.2 1 2 3 . # (7) ( 1 —丙烯基）6 —〇一儲丙氧基一 2—去氧一3 — 〇一[(R) — 3— （4 —甲氧苄氧基）癸基]一 2— (2，2， 2—三氯乙氧羰胺基）一 α— D -吡喃葡糖苷將市售（1，5 —環辛基二烯）雙（甲二苯膦）銥六氟磷酸鹽（ 365 mg，0.432 mmol)溶在四氫呋喃（40mL)，進行氫取代以活化銥錯合物，使紅色溶液呈透明，將反應系完全充以氮氣。溶液中加入（6 )所得烯丙基 2 —去氧一 3 -〇一[(R) — 3— (4 —甲氧苄氧基）癸基]—2— (2，2， _ 2 —三氯乙氧羰胺基）—α — D —吡喃葡糖苷（5.7 8 g， 8.6 1 mmol )，於室温下攪拌2小時。減壓濃縮，所得混合物溶在二氯甲院（4 5 m L )，於0 °C加入吡啶（1 . 2 m L , 14.8mmol )及氯甲酸烯丙酯（1.4mL，13.2mmol )，攪拌1 小時。加入飽和碳酸氫鈉水溶液，以二氯甲烷萃取，將有機層以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，7 : 3 )，可 200413400 得標題化合物（5.85g,產率90%)。 IR vmax (CHC 1 3 ) 3 6 0 5，3 43 6，29 5 6，29 3 0, 2 8 5 9, 1 745, 1 67 8 cm-】· ]H-NMR ( 400 MHz, CDC13) δ 0.88 (3H，t, J = 6.6 Hz)， 1.26- 1.64 ( 1 5H, m), 1.7 8 - 1 . 8 1 ( 2 H，m)，3 . 3 4 ( 1 H，d，J = 2.2 Hz，〇H)，3.42-3.5 6 (3H，m)，3.7 2-3.9 8 (7H，m，含 3H，s，at 3.80 ppm), 4.33-4.46 (4H, m), 4.63-4.77 (4H? m), 5.03 (1H, d，J二 3.7 Hz)，5.12-5.21 (2H，m，含 NH)，5.26-5,40 (2H，m)， 5.95 (1H, m)，6.14 (1H，dd，J二 1.5，12.5 Hz)，6.88 (2H，d， J = 8. 1 Hz), 7.25-7.27 (2H, m). MS (FAB,陽性）m/z，776 (M + Na) +，754 (M + H) + . HRMS (ESI，陽性），計算値 CwHwChNOnNa: 776.23 5 5 ; 實測値：776.2318. (8) (1—丙燃基）6—〇一稀丙氧鑛基一2—去氧一4一〇一二烯丙膦酸基一3 —〇一[(R) — 3— （4 —甲氧苄氧基）癸基]—2— (2，2，2—三氯乙氧羰胺基）一a-D — 吡喃葡糖苷將（7 )所得（1 一丙烯基）6 -〇一烯丙氧羰基一 2 —去氧一3 —〇一 [(R) — 3—（4 —甲氧卞氧基）癸基]—2 — (2，2，2—三氯乙氧羰胺基）一 a— D —吡喃葡糖苷（ 5.7 0g，7.5 5 mmol )，依實施例1 4 ( 5 )之方法反應，可得標題化合物（5.60g，產率81% )。 IR vmax (CHCls) 3 4 3 5. 2 9 5 6? 2 9 3 K 2 85 9, 174 6, 1 67 8, 1 6 61, 16 5 1, 16 13 c iTj' 1 · 200413400 !H-NMR ( 400 MHz, CDC13) δ 0.88 (3H，t, J = 6.6 Hz), 1.22- 1.64 ( 1 5H, m), 1.7 7 - 1.84 (2H, m)5 3.4 6 ( 1 H, m), 3.58-3.75 (2H, m), 3.79 (3H, s), 3.87-4.01 (3H, m), 4.34-4.50 (5H, m), 4.55-4.74 (8H, m)5 5.05 (1H, d, 1 = 3.7 Hz), 5.14- 5.38 (8H，m，含 NH)，5.87 -5.9 8 (3 H，m)，6.13 (1H，dd， J = 2.2，12.5Hz)，6.86(2H，d，J = 8.8Hz)，7.25(2H，d，J = 8.8Hz), 4.85 (1H, d, J 2 3.7 Hz), 5.24-5.31 (2H, m) 5 5.87 (1 Η, m), 6.4 2 (1 ，, d, J 9.5 Η z), 6 · 8 6-6.90 (2 Η, m), 7.2 5 (2 Η, d, J 8.8 Hz). MS (FAB, positive) m / z, 614 (M + Na) +, 5 92 (M + H) +. HRMS (ESI, positive). Calculate 値 C29H44F3N08Na: 6 1 4.290 1; Measured 値: 6 1 4.2 9 4 3. (6) propyl 2 —deoxy 3 —〇 — [(R) — 3- (4-methoxybenzyloxy) decyl] -2- (2,2,2-trichloroethoxycarbonylamino) -α-D-glucopyranoside. 2-deoxy-3-0-[(R) — 3- (4-methoxybenzyloxy) decyl] 2-trifluoroacetamido-α-D-glucopyranoside (5.6 1g, 9.48 mmol) was dissolved in ethanol (40 mL), 1 mol / L sodium hydroxide aqueous solution (40 mL) was added, and the mixture was stirred at 8 CTC for 5 hours. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained crude amine was dissolved in tetrahydrofuran (25 mL), and a saturated aqueous sodium hydrogen carbonate solution (25 mL) and 2,2,2-trichloroethyl chloroformate (2.20 g, 10.4 mm) were added thereto. Stir for 30 minutes. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane: ethyl acetate, 2: 3) to obtain the title compound (6.01 g, yield 95%). IR vmax (KBr) 3 3 49, 3 065, 295 5, 2927, 2 85 6, 1 7 1 3, 1646, 16 14 cm " 1 · 1 Η-Ν Μ R (4 0 0 MHz, CDCJ 3) δ 0.8 8 (3 H, t, J 2 6.6 H z), 200413400 1.26- 1.80 (14 Η, m), 2.04 (1 Η, t, OH), 3.42-3.90 (1 3 H, m, including 3H, s, at 3.80 ppm), 3.99 (1H, dd, J = 6.6, 12.4 Hz), 4.19 (1H, m), 4.39, 4.44 (2H, AB-q, J = 11.0 Hz), 4.69, 4.74 (2H, AB-q, J-12.1 Hz), 4.85 (1H, d, J-3.7 Hz), 5.19-5.32 (3H, m, including NH), 5.84-5.94 (1H, m), 6.86-6.89 (2H, m ), 7.24-7.27 (2H, m). MS (FAB, positive) m / z, 692 (M + Na) +. HRMS (ESI, positive), calculate 値 C30H46Cl3NO9Na: 692.2141; found: 6 9 2.2 1 2 3. # (7) (1 -propenyl) 6-0-propoxy-2-deoxy-3-0-[(R) — 3-(4-methoxybenzyloxy) decyl]- 2- (2,2,2-trichloroethoxycarbonylamino) -α-D-glucopyranoside will be commercially available (1,5-cyclooctyldiene) bis (methyldiphenylphosphine) iridium hexafluoro Phosphate (365 mg, 0.432 mmol) was dissolved in tetrahydrofuran (40 mL) and hydrogen substituted to activate Complexes, the red solution was clear, the reaction system is completely filled with nitrogen. To the solution was added (6) the allyl 2-deoxy-3--0-[(R) — 3 -— (4-methoxybenzyloxy) decyl] —2— (2,2, — 2—tri Chloroethoxycarbonylamino) -α-D-glucopyranoside (5.7 8 g, 8.6 1 mmol), and stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting mixture was dissolved in dichloromethane compound (45 ml). Pyridine (1.2 ml, 14.8mmol) and allyl chloroformate (1.4mL, 13.2mmol) were added at 0 ° C, and the mixture was stirred. 1 hour. A saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, 7: 3) to obtain the title compound (5.85 g, yield 90%) by 200413400. IR vmax (CHC 1 3) 3 6 0 5, 3 43 6, 29 5 6, 29 3 0, 2 8 5 9, 1 745, 1 67 8 cm-] ·] H-NMR (400 MHz, CDC13) δ 0.88 (3H, t, J = 6.6 Hz), 1.26- 1.64 (1 5H, m), 1.7 8-1. 8 1 (2 H, m), 3. 3 4 (1 H, d, J = 2.2 Hz 〇H), 3.42-3.5 6 (3H, m), 3.7 2-3.9 8 (7H, m, containing 3H, s, at 3.80 ppm), 4.33-4.46 (4H, m), 4.63-4.77 (4H? m), 5.03 (1H, d, J 3.7 Hz), 5.12-5.21 (2H, m, including NH), 5.26-5, 40 (2H, m), 5.95 (1H, m), 6.14 (1H, dd , J 2 1.5, 12.5 Hz), 6.88 (2H, d, J = 8.1 Hz), 7.25-7.27 (2H, m). MS (FAB, positive) m / z, 776 (M + Na) +, 754 (M + H) +. HRMS (ESI, positive). Calculate 値 CwHwChNOnNa: 776.23 5 5; Measured 値: 776.2318. (8) (1-propane-based) 6—0 dilute propoxy-based—2— Deoxy-4,010-diallylphosphonic acid group, 3-0-[(R) —3- (4-methoxybenzyloxy) decyl] -2- (2,2,2-trichloroethyl (Oxycarbonylamino) -aD-glucopyranoside will be obtained from (7) (1-propenyl) 6-o-allyloxycarbonyl- 2 -deoxy-3 -〇-[(R)-3- (4—Methoxymethoxy) decyl] —2— (2,2,2-trichloroethoxycarbonylamino) —a—D—glucopyranoside (5.7 0 g, 7.5 5 mmol), according to Example 1 4 (5), the title compound (5.60 g, yield 81%) was obtained. IR vmax (CHCls) 3 4 3 5. 2 9 5 6? 2 9 3 K 2 85 9, 174 6, 1 67 8, 1 6 61, 16 5 1, 16 13 c iTj '1 · 200413400! H-NMR (400 MHz, CDC13) δ 0.88 (3H, t, J = 6.6 Hz), 1.22- 1.64 (1 5H, m), 1.7 7-1.84 (2H, m) 5 3.4 6 (1 H, m), 3.58- 3.75 (2H, m), 3.79 (3H, s), 3.87-4.01 (3H, m), 4.34-4.50 (5H, m), 4.55-4.74 (8H, m) 5 5.05 (1H, d, 1 = 3.7 Hz), 5.14- 5.38 (8H, m, including NH), 5.87 -5.9 8 (3 H, m), 6.13 (1H, dd, J = 2.2, 12.5Hz), 6.86 (2H, d, J = 8.8Hz ), 7.25 (2H, d, J = 8.8

Hz). MS (FAB，陽性）m/z，93 6 (M + Na) + , 914 (M + H) + · HRMS (ESI，陽性），計算値 C4〇H59Cl3N〇i4PNa: 936.2636 •，實測値：93 6.2639· (9) 6— ◦一稀丙氧羯基一 2—去氧一 4一〇一一嫌丙膦酸基一3—〇一 [(R) — 3— (4 —甲氧节氧基）癸基]—2 一（2，2，2 —三氯乙氧羯胺基）—D —卩比喃葡糖將（8)所得（1 一丙烯基）6— 0 —烯丙氧羰基一 2—去氧—4一〇—二烯丙膦酸基—3 —〇一 [(R) — 3— (4 —甲氧苄氧基）癸基]一 2—（2，2，2-三氯乙氧羰胺基）一 α —D _吡喃葡糖苷（5.55g, 5.7 lmmol )，依實施例14 ( 6 )之方法反應，可得標題化合物（4.60g，產率92% ) ° IR vmax (CHC 1 3 ) 3 6 9 1，3 600，34 3 5，295 5，293 2，2 85 8，1 747, 16 11 cm"1 · 4 - NMR ( 500 MHz，CDC13 ) δ 0 · 8 8 ( 3 H，t，J = 6.8 H z )， 1.26-1.5 5 (12H，m)，1.77-1.81 (2H，m)，3·45 (1H，m), 3.53 (1H，brs，OH)，3.62-3.7] (2H，m)，3.79 (3 H，s)，3.86-3.91 (2 H，m), 4 . 1 6 ( 1 H …m ), 4 · 2 9 - 4.4 3 (4 H，m ): 4.5 卜 4 · 6 3 ( 8 H， 200413400 m)，4.72 (1H，AB-q, J二 11.7 Hz), 5.22- 5.3 8 (8H，m，含 NH)， 5.8 8 - 5.9 7 (3 H, m), 6.86 (2H, d, J-7.8 Hz), 7.25 (2H, d, J = 8.8 Hz). MS (FAB,陽性）m/z，8 9 6 (M + Na) +，874 (M + H) + . HRMS (ESI，陽性），計算値·037Η55〇13Ν〇14ΡΝη: 8 9 6.23 20 ;實測値：8 9 6 · 2 3 4 9 · (10) 2 —（二烯丙膦酸氧基）乙基6 —〇一 {6 —〇一烯丙氧羰基一 2—去氧一4一〇一二烯丙鱗酸基一3 —〇一[(R )一3一（4一甲氧苄氧基）癸基]一 2一（2，2，2一三氯乙氧羰胺基）一 β— D —吡喃葡糖基丨一 2，3 —二一〇一十二基一 α - D —吡喃葡糖苷（第C b 1工程）將（9)所得6—〇一烯丙氧羰基一 2 —去氧一 4 一〇一二 0丙膦酸基一 3—〇一[(R) — 3— (4 —甲氧予氧基）癸基]—2 —（2，2，2 —三氯乙氧羰胺基）一 D —吡喃葡糖（ 7l〇mg，0.8 12mmol)及實施例1 0 ( 5 )所得2 —（二烯丙膦酸氧基）乙基2，3 —二一〇—十二基一α—D —吡喃葡糖苷 (400mg, 0.5 5 5mmol )，依後述實施例1 6 ( 6 )之方法反應，可得標題化合物（5 89mg，產率67% )。 IR vmax (CHC13) 2928, 2856, 1 745，1612 cm-1· ifi-NMR ( 500 MHz, CDC13) δ 0·88 (9H，t，J二6.8 Hz)， ^ 25 - 1.5 8 (52H，m)，1.74- 1.85 (2H，m)，2.48 (1H，d，J = 2.9 Hz，〇H)，3.24 (1H，dd，J = 2.9，9.8 Hz)，3.28 (1H，m)，3.33 (]H, td, 1 = 9.8, 2.9 Hz), 3.45-3.5 3 ( 3 H, m), 3.5 7-3.66 (4H, m ) , 3 . 7 .1 - 3 . 7 7 ( 2 I-I，m )，3 . 7 9 ( 3 H . s)，3 . 8 4 - 3.9 3 ( 5 H , m)， -]73 200413400 4·10 (1H，d，J = 8.8 Ηζ)，4·19-4·36 (4H，m)，4.4 1 (2H，s)， 4.5 1- 4.60 (1 OH，m)，4.63 (2H, d, J = 5.9 Hz)，4·74 (1H，ABq， J=12.7 Hz)，4.81 (1H，d，7.8 Hz)，4.90 (1H，d，2.9Hz). MS (FAB, positive) m / z, 93 6 (M + Na) +, 914 (M + H) + · HRMS (ESI, positive), calculated 値 C4〇H59Cl3N〇i4PNa: 936.2636 •, measured 实: 93 6.2639 · (9) 6- ◦ a dilute propoxyfluorenyl group 2-deoxy 4 10-1-propylphosphonic acid group 3-0-[(R) — 3 — (4 —methoxy section (Oxy) decyl] -2 mono (2,2,2-trichloroethoxyamido) -D-pyranoglucose (8) to obtain (1 monopropenyl) 6-0-allyloxy Carbonyl- 2 -deoxy-4 -10-diallylphosphonic acid -3 -0-[(R)-3-(4-methoxybenzyloxy) decyl]-2-(2, 2, 2 -Trichloroethoxycarbonylamino) -α-D-glucopyranoside (5.55g, 5.7 lmmol), and reacted according to the method of Example 14 (6) to obtain the title compound (4.60g, yield 92%) ° IR vmax (CHC 1 3) 3 6 9 1, 3 600, 34 3 5, 295 5, 293 2, 2 85 8, 1 747, 16 11 cm " 1 · 4-NMR (500 MHz, CDC13) δ 0 8 8 (3 H, t, J = 6.8 H z), 1.26-1.5 5 (12H, m), 1.77-1.81 (2H, m), 3.45 (1H, m), 3.53 (1H, brs, OH), 3.62-3.7] (2H, m), 3.79 (3 H, s) , 3.86-3.91 (2 H, m), 4. 1 6 (1 H… m), 4 · 2 9-4.4 3 (4 H, m): 4.5 BU 4 · 6 3 (8 H, 200413400 m), 4.72 (1H, AB-q, J 2 11.7 Hz), 5.22- 5.3 8 (8H, m, including NH), 5.8 8-5.9 7 (3 H, m), 6.86 (2H, d, J-7.8 Hz) , 7.25 (2H, d, J = 8.8 Hz). MS (FAB, positive) m / z, 8 9 6 (M + Na) +, 874 (M + H) +. HRMS (ESI, positive), calculate 値· 037Η55〇13Ν〇14ΡΝη: 8 9 6.23 20; Found 値: 8 9 6 · 2 3 4 9 · (10) 2-(diallylphosphonic acidoxy) ethyl 6-〇-1 {6--0-ene Propoxycarbonyl- 2 -deoxy-4 10-diallyl phosphono- 3 -0-[(R)-3-(4-methoxymethoxybenzyloxy) decyl]-2-(2, 2 2,2-trichloroethoxycarbonylamino) -β-D-glucopyranosyl-1,2-dioxoyl-12-yl-α-D-glucopyranoside (Project C b 1) Add the obtained 6-allyloxycarbonyl- 2 -deoxy-4 10-12 propylphosphonic acid -3--0-[(R)-3- (4-methoxymethoxy) obtained in (9) Decyl] -2- (2,2,2-trichloroethoxycarbonylamino) -D-glucopyranose (7lOmg 0.8 12 mmol) and 2- (diallylphosphonic acidoxy) ethyl 2,3-dioxo-dodecyl-α-D-glucopyranoside (400 mg, 0.5 5) obtained in Example 10 (5) 5 mmol), and reacted according to the method of Example 16 (6) described later to obtain the title compound (5 89 mg, yield 67%). IR vmax (CHC13) 2928, 2856, 1 745, 1612 cm-1 · ifi-NMR (500 MHz, CDC13) δ 0 · 88 (9H, t, J = 6.8 Hz), ^ 25-1.5 8 (52H, m ), 1.74- 1.85 (2H, m), 2.48 (1H, d, J = 2.9 Hz, 0H), 3.24 (1H, dd, J = 2.9, 9.8 Hz), 3.28 (1H, m), 3.33 () H, td, 1 = 9.8, 2.9 Hz), 3.45-3.5 3 (3 H, m), 3.5 7-3.66 (4H, m), 3.7 .1-3. 7 7 (2 II, m), 3. 7 9 (3 H. S), 3. 8 4-3.9 3 (5 H, m),-] 73 200413400 4 · 10 (1H, d, J = 8.8 Ηζ), 4.19-4 · 36 (4H, m), 4.4 1 (2H, s), 4.5 1- 4.60 (1 OH, m), 4.63 (2H, d, J = 5.9 Hz), 4.74 (1H, ABq, J = 12.7 Hz) , 4.81 (1H, d, 7.8 Hz), 4.90 (1H, d, 2.9

Hz)，5.2 卜 5.39 (10H，m)，5.87-5.97 (5H，m)，6.41 (1H，d, J 二 6.8 Hz·，NH)，6.86 (2H，d，J= 8.8 Hz)，7·26 (2H，d，J二 7.8Hz), 5.2, 5.39 (10H, m), 5.87-5.97 (5H, m), 6.41 (1H, d, J 2 6.8 Hz ·, NH), 6.86 (2H, d, J = 8.8 Hz), 7 · 26 (2H, d, J II 7.8

Hz). MS (FAB，陽性）m/z 1 6 1 4 (M + K) +，1 5 9 8 (M + N a) + · HRMS (ESI,陽性），計算値 C75H126Cl3N023P2Na: 1 5 9 8.7 1 50;實測値：1 5 9 8.7 1 3 3 . (11) 2—（二烯丙膦酸氧基）乙基6 —〇一 {6 —〇一烯丙氧羯基一 2—去氧一 4一〇一二;)¾丙膦酸基一3 —〇一[(R )一3一（4 一甲氧苄氧基）癸基]—2 — [(Z) — 11 -十八碳;^希醯胺基]一 β— D — 口比喃蔔糖基丨一 2，3—二一〇一十一基一 a— D —吡喃葡糖苷（第Cb2工程）將（1 0 )所得化合物（5 7 0 m g，0.3 6 1 m m ο 1 )，依後述實施例16 ( 7 )之方法反應，可得標題化合物（3 80mg,產率 63% )。 IR vmax (CHC 1 3 ) 3 5 8 8，345 3，3 3 1 1 , 3089，2928，2 85 6，1 748, 1 6 6 4 cm"1 · 1 H-NMR ( 500 MHz，CDC13 ) δ 0 · 8 8 ( 1 2 H，t，J = 6.8 H z)， 1 . 1 8 - 1 · 6 0 ( 7 4 H，m), 1 · 7 4 - 1 · 8 4 ( 2 H，ni)，1 · 9 9 - 2.0 2 (4 H，m)， 2.05-2.15 (2H，m)，2.82 (1H, s，〇H), 3.12 (1H，m)，3.23 (1H，dd，J:3.9, 9.8 Hz), 3.34 (1H，t，J = 9.8 Hz)，3.44-3.52 (3 H , m ), 3.57 ( ] H , m ), 3.6 3 - 3.7 4 ( 5 H , m), 3.7 6 - 3.8 5 ( 6 H ? 200413400 m，含 3H，s，at 3.79 ppm)，4.05-4.10 (2H，m)，4.15-4.34 (4H， ni), 4.41 (2H, s), 4.51-4.57 (10H, m), 4.62 (2H, d, J = 5.9 Hz), 4.88 (1H, d, J = 3.9 Hz), 5.13 (1H, d, J = 7.8 Hz), 5.20-5.40 (12H，m)，5.86-5.98 (5H，m)，6.60 (1H，d，J = 7.8 Hz， N H )，6 · 8 6 ( 2 H , d，J 二 8.8 H z)，7 · 2 4 ( 2 H，d，J = 7 · 8 H z). MS (FAB，陽性）m/z 1704 (M + K) + , 1688 (M + Na) + . HRMS (ESI，陽性），計算値 c9〇H157N〇22P2Na: 1689.0565 ;實測値：1 6 8 9.0 5 5 7 · (12) 2 —（二燃丙膦酸氧基）乙基6 —〇一{6 —〇一稀丙氧羰基—2 一去氧—4一〇一二烯丙膦酸基一 3— ◦一 [( R )一 3-羥癸基]—2 - [(Z) — 11-十八碳烯醯胺基]—β -D —吡喃葡糖基}— 2，3 —二一 ◦一十二基一 a— D —吡喃葡糖苷（第Cb4工程）將（1 1 )所得化合物（3 62mg，0.217mm〇l )溶在二氯甲烷（5mL)，加入水（0.5 mL)及 2，3 - 二環一 5，6 —二氰基—1，4 —醌（D D Q，6 lmg，0.26 8mmol )，於室温下攪拌1小時。反應液以二氯甲烷稀釋，以飽和碳酸氫鈉水溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以砂膠柱層析純化（己院：乙酸乙酯，3 : 7 )，可得標題化合物（266mg,產率79% )。 IR vmax (CHC13) 3452，33 2 3，3089，2928，2856，1748，1663 cm"1 · 】H_NMR ( 500 MHz，CDC13 ) δ 0 · 8 8 ( ] 2 H，t，J 二 6.8 H z )，Hz). MS (FAB, positive) m / z 1 6 1 4 (M + K) +, 1 5 9 8 (M + N a) + · HRMS (ESI, positive), calculate 値 C75H126Cl3N023P2Na: 1 5 9 8.7 1 50; Measured fluorene: 1 5 9 8.7 1 3 3. (11) 2- (diallylphosphonic acidoxy) ethyl 6—〇— {6—〇 allyloxyfluorenyl—2—deoxy— 4 10-12;) ¾ phosphono- 3-0-[(R) 3-(4-methoxybenzyloxy) decyl]-2-[(Z)-11-octadecyl; ^ Hisamino] -β-D-O-pyranosyl group- 2,3-210110-yl-a-D-glucopyranoside (Project Cb2) will be obtained by (1 0) The compound (570 mg, 0.3 61 mm) was reacted according to the method of Example 16 (7) described later to obtain the title compound (3 80 mg, yield 63%). IR vmax (CHC 1 3) 3 5 8 8, 345 3, 3 3 1 1, 3089, 2928, 2 85 6, 1 748, 1 6 6 4 cm " 1 · 1 H-NMR (500 MHz, CDC13) δ 0 · 8 8 (1 2 H, t, J = 6.8 H z), 1. 1 8-1 · 6 0 (7 4 H, m), 1 · 7 4-1 · 8 4 (2 H, ni) , 1. 9 9-2.0 2 (4 H, m), 2.05-2.15 (2H, m), 2.82 (1H, s, 0H), 3.12 (1H, m), 3.23 (1H, dd, J: 3.9 , 9.8 Hz), 3.34 (1H, t, J = 9.8 Hz), 3.44-3.52 (3 H, m), 3.57 (] H, m), 3.6 3-3.7 4 (5 H, m), 3.7 6- 3.8 5 (6 H? 200413400 m, including 3H, s, at 3.79 ppm), 4.05-4.10 (2H, m), 4.15-4.34 (4H, ni), 4.41 (2H, s), 4.51-4.57 (10H, m), 4.62 (2H, d, J = 5.9 Hz), 4.88 (1H, d, J = 3.9 Hz), 5.13 (1H, d, J = 7.8 Hz), 5.20-5.40 (12H, m), 5.86- 5.98 (5H, m), 6.60 (1H, d, J = 7.8 Hz, NH), 6 · 8 6 (2 H, d, J = 8.8 H z), 7 · 2 4 (2 H, d, J = 7 · 8 H z). MS (FAB, positive) m / z 1704 (M + K) +, 1688 (M + Na) +. HRMS (ESI, positive), calculated 値 c9〇H157N〇22P2Na: 1689.0565; found値: 1 6 8 9.0 5 5 7 · (12) 2 — (Second combustion Phosphonic acidoxy) ethyl 6-0- {6-0-dilute propoxycarbonyl-2 2-deoxy-4-10-diallylphosphonic acid 3-3- ◦-[(R) -3-hydroxydecyl Group] —2 — [(Z) —11-octadecenylamino] —β-D—glucopyranosyl} —2,3—dione—dodecyl—a—D—pyran Glucoside (Cb4 project) The compound (3 62 mg, 0.217 mm) obtained in (1 1) was dissolved in dichloromethane (5 mL), and water (0.5 mL) and 2,3 -bicyclo-5,6- Dicyano-1,4-quinone (DDQ, 61 mg, 0.26 8 mmol) was stirred at room temperature for 1 hour. The reaction solution was diluted with dichloromethane, washed with a saturated sodium bicarbonate aqueous solution and a saturated saline solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Guiyuan: ethyl acetate, 3: 7) to obtain the title compound (266 mg, yield 79%). IR vmax (CHC13) 3452, 33 2 3, 3089, 2928, 2856, 1748, 1663 cm " 1 ·】 H_NMR (500 MHz, CDC13) δ 0 · 8 8 (] 2 H, t, J 6.8 H z) ,

1 · 2 5 - 1 . 7 3 ( 7 6 H，ni)，1 · 9 9 - 2 · 0 1 ( 4 H，m )，2.2 0 ( 2 H，t，j、7 I 200413400 6.8 Ηζ)，3·23 (1H, dd，J = 3.9，9·8 Hz)，3.26 (1H，brs5 OH), 3.3 1 (1H，t，J = 9.8，8.8 Hz)，3.45 (1H，t，J = 9.8, 8.8 Hz)， 3.49-3.87 (13H，m)，4.12-4.19 (3H，m)，4.23-4.37 (3H，m)， 4.51-4.58 (10H，m)，4.62 (2H，d，J = 5.9 Hz)，4.86 (1H，d， J = 3.9 Hz)，5.10 (1H，d，J = 8.8 Hz)，5·24-5·41 (12H，m)， 5.89-5.99 (5H，m)，7.09 (1H，brs, NH). MS (FAB，陽性）m/z 1 5 8 4 (M + K) +，1 5 6 8 (M + N a) + · HRMS (ESI，陽性），計算値 C82H149N〇2iP2Na: 1 568.9993 •，實測値：1 5 6 8.9 9 9 1 . · (13) 2 —膦酸氧乙基6 — ◦ — {2 —去氧一3 —〇一[(R )—3 —羥癸基]—2— [(Z) - 11一十八碳烯醯胺基]—4 — 〇一膦酸基一 β — D —吡喃葡糖基} 一 2，3 —二一〇一十二基一 a— D -吡喃葡糖苷（第Cb3工程）將（1 2 )所得化合物（2 4 0 m g，0.1 5 5 m m ο 1 )，依後述實施例16 ( 8 )之方法反應，可得標題化合物（IMmg，產率 86% )。 IR vmax (ΚΒι.) 3 232，3006，295 5，292.4，285 3，2326 cm-1 · · 1 H-NMR ( 500 MHz，CDC13 ) δ 0.9 0 ( 1 2 H，t，J 二 6.8 H z)， 1.29- 1.75 (76H, m), 2.01-2.04 (4H, m), 2.26 (2H, t, J = 7.8 Hz), 3.20 (1H, dd, J-3.9, 9.8 Hz), 3.34-3.40 (2H? m), 3.47 (1H, t, J-9.8, 8.8 Hz)? 3.51-3.57 (2H, m), 3.64-3.87 (12H, m), 3.93 (1H; m), 4.06-4.16 (4H, m), 4.49 (1H, d, J = 8.8 Hz), 4.92 ( 1 H , d , J - 3 . 9 Hz), 5.31-5.37 ( 2 H , m ). MS (ESI,陰性）m/z 1 3 00 (M-H)'. -176 - 200413400 HRMS (ESI，陰性），計算値 C66H128N〇〗9P2: 1 300.8 5 60 ;實測値：1 3 0 0.8 5 7 2 . 〔實施例1 6〕一氨憐酸（6 —〇一{2—去氣一3 —〇一[(R) — 3 —甲氧癸基]—2 — [( Z ) — 1 1 一十八碳烯醯胺基]—4 一〇—膦酸基一β— D —吡喃葡糖基}— 2，3 —二一〇一十二基一 α — D —吡喃葡糖基）乙酯 (1) 3— (4，6—〇一亞異丙基一 a — D — Π比喃葡糖基） —1—丙烷（第Eal工程） _ 將3—（四一〇一乙醯基一α—D — D比喃葡糖基）一 1 — 丙烷（Car bohydr. Res·，184，221—229(1988)，已知化合物）（4.75g, 12.8mmol)溶在乙醇（100mL)，加入氫氧化鉀（5 3 m g，0.9 4 6 m m ο 1 )，於室温下攪拌2小時，將反應液減壓濃縮乾燥。所得殘渣溶在二甲基甲醯胺（ 50mL )，加入2—甲氧丙烷（2.5mL，26.1mmol)及對甲苯磺酸（485mg, 2.5 5mmol )，於室温下攪拌2小時。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，2 : 3 ) ， · 可得標題化合物（2.34g，產率75%)。 IR vmax (CHC1 3 ) 3 67 5，3 602, 346 9，308 1，2945，2909，1 7 3 2， 1 67 2，1 643 cm-1· ^-NMR ( 500 MHz, CDC13) δ 1.44 (3H，s)，1.50 (3H，s), 2.42-2,56 (2H，m)，2.85 (1H，brs，〇H)，3.02 (1H，brs，〇H)， 3.4 3 - 3 · 5 0 ( 2 H，m )，3 · 6 8 ( 1 H，t，J 二 9 · 8 H z )，3.7 3 ( 1 H，t， J 二 8 · 8 H z )，3 . 8 2 ( 1 H，d d .J 二 5.9 , 9.8 H z.)，3 . 8 7 ( ] H，m)，4 . 1 2 177 200413400 5.80 (1H，m)· (1H，m)，5.09-5.17 (2H，m) MS (FAB，陽性）m/z，⑹（M + Na) +，245 (m + h) + . (2) 3— (2，3 —二—〇一十二基—4, 6 —〇—亞異丙基一 01一 D —啦喃葡糖基）一 1 一丙烷（第E a 2工程）將（1 )所得化合物（2 · 3 〇 g , 9 · 4 2 m ηΊ 0丨）溶在二甲基甲醯胺（3 0 m L ) ’於冰冷却下加入氫化鈉（6 0 %油性，9 6 3 m g， 24. 1 mmol )，攪拌1 5分後，加入+二碳溴（5 .丨5 g， 2〇.7mmol) ’於室温下攪拌3小時。加入水以中止反應，1 · 2 5-1. 7 3 (7 6 H, ni), 1 · 9 9-2 · 0 1 (4 H, m), 2.20 (2 H, t, j, 7 I 200413400 6.8 Ηζ), 3 · 23 (1H, dd, J = 3.9, 9.8 Hz), 3.26 (1H, brs5 OH), 3.3 1 (1H, t, J = 9.8, 8.8 Hz), 3.45 (1H, t, J = 9.8 , 8.8 Hz), 3.49-3.87 (13H, m), 4.12-4.19 (3H, m), 4.23-4.37 (3H, m), 4.51-4.58 (10H, m), 4.62 (2H, d, J = 5.9 Hz), 4.86 (1H, d, J = 3.9 Hz), 5.10 (1H, d, J = 8.8 Hz), 5.24-5 · 41 (12H, m), 5.89-5.99 (5H, m), 7.09 (1H, brs, NH). MS (FAB, positive) m / z 1 5 8 4 (M + K) +, 1 5 6 8 (M + N a) + · HRMS (ESI, positive), calculate 値 C82H149N 〇2iP2Na: 1 568.9993 •, Found 値: 1 5 6 8.9 9 9 1. · (13) 2 —phosphonooxyethyl 6 — ◦ — {2 —deoxy-3 —〇 — [(R) —3 — Hydroxydecyl] -2 — [(Z) -11 octadecenylamino] -4—〇-phosphono-β-D-glucopyranosyl} -2,3-dione Dodecyl-a-D-glucopyranoside (Project Cb3) The compound (2 40 mg, 0.1 5 5 mm ο 1) obtained in (1 2) will be described later. The method of Example 16 (8) was reacted to obtain the title compound (IMmg, yield 86%). IR vmax (KB). 3 232, 3006, 295 5, 292.4, 285 3, 2326 cm-1 · · 1 H-NMR (500 MHz, CDC13) δ 0.9 0 (1 2 H, t, J 2 6.8 H z ), 1.29- 1.75 (76H, m), 2.01-2.04 (4H, m), 2.26 (2H, t, J = 7.8 Hz), 3.20 (1H, dd, J-3.9, 9.8 Hz), 3.34-3.40 ( 2H? M), 3.47 (1H, t, J-9.8, 8.8 Hz)? 3.51-3.57 (2H, m), 3.64-3.87 (12H, m), 3.93 (1H; m), 4.06-4.16 (4H, m), 4.49 (1H, d, J = 8.8 Hz), 4.92 (1 H, d, J-3.9 Hz), 5.31-5.37 (2 H, m). MS (ESI, negative) m / z 1 3 00 (MH) '. -176-200413400 HRMS (ESI, negative). Calculate 値 C66H128N〇 9P2: 1 300.8 5 60; Measured 値: 1 3 0 0.8 5 7 2. [Example 1 6] Ammonia Acid (6 —〇— {2—Degassing—3—〇 — [(R) — 3 —Methoxydecyl] —2 — [(Z) — 1 1 Octadecenylamino] -4— 〇-phosphono-β-D-glucopyranosyl} -2,3-dioxoyl-α-D-glucopyranosyl) ethyl (1) 3- (4,6 —〇—Isopropylidene—a — D — Gluconosyl) —1-propane (Eal Project) _ Will be 3— (4101B -Α-D — D glucopyranosyl) — 1 —propane (Car bohydr. Res., 184, 221-229 (1988), known compound) (4.75 g, 12.8 mmol) was dissolved in ethanol (100 mL) Then, potassium hydroxide (5 3 mg, 0.9 4 6 mm ο 1) was added, and the mixture was stirred at room temperature for 2 hours, and the reaction solution was concentrated and dried under reduced pressure. The obtained residue was dissolved in dimethylformamide (50 mL), 2-methoxypropane (2.5 mL, 26.1 mmol) and p-toluenesulfonic acid (485 mg, 2.5 5 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, 2: 3) to obtain the title compound (2.34 g, yield 75%). IR vmax (CHC1 3) 3 67 5, 3 602, 346 9, 308 1, 2945, 2909, 1 7 3 2, 1, 67 2, 1 643 cm-1 · ^ -NMR (500 MHz, CDC13) δ 1.44 ( 3H, s), 1.50 (3H, s), 2.42-2, 56 (2H, m), 2.85 (1H, brs, 0H), 3.02 (1H, brs, 0H), 3.4 3-3 · 5 0 (2 H, m), 3 · 6 8 (1 H, t, J 2 9 · 8 H z), 3.73 (1 H, t, J 2 8 · 8 H z), 3. 8 2 (1 H , Dd .J 5.9, 9.8 H z.), 3. 8 7 (] H, m), 4. 1 2 177 200413400 5.80 (1H, m) · (1H, m), 5.09-5.17 (2H, m ) MS (FAB, positive) m / z, ⑹ (M + Na) +, 245 (m + h) +. (2) 3— (2,3—two—120-based base—4, 6—〇 —Isopropylidene—01—D—Gluranosyl) —1—Propane (E a 2nd Project) The compound (1) obtained in (1) (2 · 3 0 g, 9 · 4 2 m ηΊ 0 丨) was dissolved Add dimethylformamide (30 ml) to ice-cooled sodium hydride (60% oily, 96.3 mg, 24.1 mmol), and stir for 15 minutes, then add + dicarbon bromide (5 (5 g, 20.7 mmol) was stirred at room temperature for 3 hours. Add water to stop the reaction,

以乙酸乙酯萃取’將有機層以水及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，9 5 : 5 )，可得標題化合物（3.4 0 g，產率6 2 % 〇 IR vmax (CHCI3) 2927, 2855, 1 6 4 2 cm"1 · !H-NMR ( 500 MHz, CDCh) δ 0.88 (6H, t, J = 6.8 Hz), 1.26-1.56 (46H，m,含 3H, s, at 1.40, 3 H, s, 1.48 ppm)， 2.39-2.50 (2H, m), 3.37 (1H, t, J = 8.8 Hz), 3.41-3.46 (2H, m), 3.49-3.56 (2H, m), 3.59-3.65 (3H, m), 3.71 (1H5 m), 3.81 (1H，dd，J = 4.9，10.7 Hz), 4.06 (1H，m)，5.06-5.14 (2H， m)，5.78 (1H, m). MS (FAB,陽性）m/z，619 (M + K) +，603 (M + Na) +，579 (ΜΗ)' H R M S (E S I,陽性），計算値 C 3 6 H 6 8 〇 5 N a : 6 0 3.4 9 7 2 ;實測値：603.4953. (3 ) 2 — ( 2，3 —二一〇一十二基一 4，6 —〇一亞異丙 -178 - 200413400 基一 α — D —吡喃葡糖基）乙醇（第E a 3工程）將（2 )所得化合物（3.25g，5.59mmol )溶在丙酮（ 4 0 m L )，加入水（1 0 m L )，過碘酸鈉（3.5 2 g，1 6.5 m m ο 1 ) 及四氧化鎢（2 · 5%第三丁醇溶液，2.0mL，0. 160mmol )，於室温下攪拌2小時。加入飽和硫代硫酸鈉水溶液，以乙酸乙酯萃取5次，以飽和碳酸氫鈉水溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，所得殘渣溶在乙醇 (4 0 m L )，於冰冷卻下加入硼氫化鈉（2 5 5 m g，6.7 4 m m ο 1 )，於室温下攪拌3 0分。反應液中加入飽和氯化銨水溶液以中止反應，以乙酸乙酯萃取3次，將有機層以飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，7 : 3 )，可得標題化合物（1.61g, 產率4 9 % )。 IR vmax (KBr) 3 522, 299 8, 29 54, 29 1 9, 285 1 cm"1 · iH-NMR ( 500 MHz, CDC13 ) δ 0.88 (6H, t, J-6.8 Hz), 1.26-1.33 (36H, m), 1.40 (3H, s), 1.48 (3H, s), 1.52-1.58 (4H，m)，1.93-1.97 (2H，m)，2.21(lH，t，J = 5.9-4.9Hz，〇H), 3.38 (1H，t，J二 8.8 Hz)，3.42-3.49 (2H，m)，3.52-3.57 (2H， m), 3.60-3.82 (7H, m), 4.20 (1H, m). MS (FAB,陽性）m/z，623 (M + K) +，607 (M + Na) +，585 (M + H) + . HRMS (ESI，陽性），計算値 C35H6806Na: 607.493 2 ;實測 fit ： 607.4 8 8 5. (4 ) ( 2，3 —二--〇一十二基一4，6 —〇一亞異丙基一 -179 - 200413400 α 一 D —吡喃葡糖基）乙基磷酸二烯丙酯（第E a 4工程）將（3 )所得化合物（5 3 0 m g，0.9 0 6 m m ο 1 )溶在四氫呋喃 (5 m L )，加入 1 Η —四 Π坐（8 3 m g，1 . 1 8 m m ο 1 )及雙（燒丙氧基）（二異丙胺基）膦（25 Omg，1.01 mmol )，於氮氣及室温下攬拌2小時。於〇 °C下冷却’加入3 0 %過氧化氫水 (0.5 mL )，攬拌1小時，加入飽和硫代硫酸鈉水溶液，以乙酸乙酯萃取3次。有機層以飽和碳酸氫鈉及飽和食鹽水依次洗浄，於硫酸鎂下乾燥，減壓蒸除溶劑，以砂膠柱層析純化（己烷：乙酸乙酯，7 : 3 )，可得標題化合物（ 619 mg,產率 92%)。 IR vmax (CHC13) 2927, 2 8 5 5 cm'1 · ^-NMR ( 400 MHz, CDC13) δ 0 · 8 8 ( 6 Η，t，J = 6.6 - 7 · 3 Η z), 1.22- 1.26 (3 6H, m), 1.39 (3H, s), 1.47 (3H, s), 1.51-1.54 (4H, m), 2.03 -2.08 (2H, m), 3.31-3.73 (9H, m), 3.81 (1H, dd, J = 5.1, 11.0 Hz), 4.08-4.20 (3H, m), 4.52-4.56 (4H, m), 5.19-5.39 (4H, m), 5.90-5.99 (2H, m). MS (FAB,陽性）m/z，7 8 3 (M + K) +，7 67 (M + Na) +，745 (M + H) + . HRMS (ESI，陽性），計算値 C41H77〇9Na: 767.5208 ;實測値：7 6 7 · 5 1 8 9 · (5) (2，3—二一〇一十二基一 α—D —吡喃葡糖基）乙基磷酸二烯丙酯（第E a 5工程）將（4 )所得化合物（6 0 5 m g , 0.8 1 3 m m ο 1 )溶於8 0 %乙酸水溶液（1 OmL )，於60°C攪拌1小時。將反應液減壓濃縮 ίδΟ - 200413400 ，以乙酸乙酯稀釋，以飽和碳酸氫鈉水溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，1 : 9 )，可得標題化合物（4 62mg，產率8 1 % )。 IR vmax (CHC13 ) 3 5 94，3446，2928，285 6 cm·1 · ^-NMR ( 500 MHz, CDC13) δ 0 · 8 8 ( 6 H，t，J = 6.8 H z ), 1.26- 1.3 1 (3 6H, m), 1.52- 1.5 8 (4H, m), 1.87 (1H, m), 2.06 (1H, m), 3.17 (1H, d, OH), 3.28 (1H, m), 3.44- 3.68 ( 8H, m, 含〇H)，3.79 (1H，m)，3.98 (1H，m)，4.12 (1H, m)，4·18 φ (1H，m)，4.38 (1H，m)，4.54-4.57 (4H，m)，5.25 -5.3 9 (4H, m), 5.91-5.98 (2H, m). MS (FAB,陽性）m/z，743 (M + K) +，727 (M + Na) +，705 (M + H) + . HRMS (ESI，陽性），計算値 C38H7409P: 705.5070 ;實測値 :705.5072. (6) (6 —〇一{2 —去氧一4 —〇一二烯丙膦酸基—3 — 〇一[(R) — 3 —甲氧癸基]—6 —〇一甲基一2— [(2，2, · 2-三氯乙氧羰基）胺基]一 β — D —吡喃葡糖基丨一 2，3 — 二一〇一十二基一 α—D —毗喃葡糖基）乙基磷酸二烯丙酯 (第E b 1工程）將2 —去氧一 4 —〇一二烯丙膦酸基一 3 一〇一 { (R) —3 —甲氧癸基} — 6 —〇一甲基一2— (2，2，2 —三氯乙氧羰胺基）—D —吡喃葡糖（美國專利第5 9 3 5 9 3 8號，已知化合物）（5 6 0 in g，0.8 0 1 m m ο 1 )溶在二氯甲院（5 m L ) -181 - 200413400 ，加入二氯乙腈（〇 . 4 m L , 3.9 9 m m ο 1 )及碳酸鉋（5 3 m g， 0. ] 61mmol )，於室温下攪拌1小時。以二氯甲烷稀釋，以飽和碳酸氫鈉水溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥，減壓蒸除溶劑。將所得粗亞胺酸酯體溶在二氯甲烷（ 5mL)，加入（5)所得化合物（ 283 mg，0.401 mmol)及分子篩只4 A ( 420mg)，於氮氣及室温下攪拌3 0分。將反應液於〇°C下冷却，加入三氟甲磺酸鹽（5pL，0.〇28mmol) ，攪拌1小時。加入飽和碳酸氫鈉水溶液以中止反應，以二氯甲烷萃取。將有機層以水及飽和食鹽水洗浄，減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，1 : 4)，可得標題化合物（3 12mg，產率56% )。 IR vmax (CHC13 ) 3 2 6 8，3 08 8，2928，28 5 6，1 7 3 8 cm"1 · ]H-NMR ( 500 MHz, CDC13) δ 0 · 8 8 ( 9 H，t，J = 6 · 8 H z)， 1.14-1.79 (54H, m), 1.88 (1H, m), 1.98 (1H, m), 2.90 (1H, d，J二2.9 Hz，〇H)，3.22-3.3 8 (7H, m，含 3H，s，at 3.27 ppm)， 3.39 (3H，s)，3.44-3.5 8 (5H，m)，3·63 (1H，dd，J = 4.9，10.7 Hz)，3.69-3.79 (7H，m)，3·97 (1H，d, J 二 11.7 Hz)，4.12-4.19 (2H,m)，4.28(lH，q，J = 9.8，8.8Hz),4.35(lH，m)，4.52-4.60 (8H, m), 4.71 ( 1 H，d , J = 8.8 H z ), 4.6 6，4.8 2 ( 2 H，A B q， J=ll.7 Hz)，5.24-5.39 (8H，ni)，5.90-5.98 (4H，m)，7.17 (1H，d，J = 7.8 Hz，NH). MS (FAB，陽性）m/z，1 422 (M + K) +，1406 (M + Na) + · HRMS (ESI，陽性），計算値 C65Hi18Cl3N〇19P2Na: 1406.6727 ;實測値：1406.6704. 182 200413400 (7) (6 —〇—{2 —去氧一4 —〇一二j：希丙膦酸基—3 — 〇一[(R) — 3 —甲氧癸基]—6 —〇一甲基一2— [(Z)— 1 1 一十八碳燏醯胺基]一 β — D —啦喃葡糖基丨—2，3 -二― 〇一十二基一 α — D —吡喃葡糖基）乙基磷酸二烯丙酯（第 E b 2工程）將（6 )所得化合物（290mg，0.210mmol )溶在四氫呋喃 (5 m L )，加入鋅粉末（270 mg，4· 1 3 mmol )及乙酸（ 0.5 m L )，於室温下攪拌2小時。濾除鋅粉後，減壓濃縮，所得殘渣以乙酸乙酯稀釋，以飽和碳酸氫鈉水溶液及飽和 _ 食鹽水洗浄，於硫酸鎂下乾燥。過濾，減壓蒸除溶劑，所得粗胺溶在二氯甲烷（5 mL )，加入（z ) - 1 1 一十八碳烯酸（71mg，0.251mmol)及 1—乙基—3— (3— 二甲胺丙基）碳化二亞胺鹽酸鹽（65mg，0.341 mmol)，於室温下攪拌24小時。反應液以二氯甲烷稀釋，以水及飽和食鹽水洗浄，於硫酸鎂下乾燥，減壓蒸除溶劑，以矽膠柱層析純化 (己烷：乙酸乙酯，1 : 4 )，可得標題化合物（158mg, 產率5 1 % )。鲁 IR Vmax (CHC13) 3454, 3 3 1 0, 2928, 28 5 6, 1 6 64 cm'1 · !H-NMR ( 500 MHz, CDCI3) δ 0.88 (12H，t，J二 6.8 Hz)， 1.26- 1.7 9 (7 6H, m), 1.90- 1.94 (2H, m), 2.00-2.01 (4H, m), 2.14-2.25 (2H, m), 3.06 (1H, d, J = 4.9 Hz, OH), 3.25-3.40 (11H，m，含 3H，s，3.28 ppm，3 H，s，3.38 ppm)，3.45-3.56 (3H, m)? 3.60- 3.6 3 ( 3 H, m), 3.67 - 3.7 7 ( 5 H, m), 3.98 (1H, t, J = 9.8 Hz), 4.0 j ( 1 H , d , J = 1 0.7 Hz), 4.11-4.21 ( 3 Η , πί ), 4.25 -183 - 200413400 (1H，q，J = 7.8 Hz)，4.54-4.59 (8H，m), 4.99 (1H，d, J = 7.8 Hz)，5.23-5.3 8 ( 1 0H, m)，5.90-5.99 (4H, m)，7.00 (1H，d, J = 7.8 Hz, NH). MS (FAB，陽性）m/z5 1512 (M + K) +，1 496 (M + Na) + . HRMS (ESI,陽性），計算値 C80H]49N〇18P2Na: 1497.0126 ；實測値：1 497.008 1 . (8) 一氫磷酸（6 —〇一{2 —去氧一3 —〇—[(r) — 3 一甲氧癸基]一 2 — [( Z ) — 1 1 —十八碳烯醯胺基]一 4 _〇一膦酸基一 β— D —D比喃葡糖基}一2，3—二一〇一十二基一 α — D -吡喃葡糖基）乙酯（第E b 3工程）將（7)所得化合物（145mg，〇.〇98mmol)溶在四氫呋喃 (5mL)，加入三苯膦（13 mg，0.051 mmol)，三乙胺（ 70μΙ^，0.502m mol)，甲酸（38μί，l.Olmmol)及肆三苯膦鈀（6mg，0.005mmol )，於氮氣及5 0 °C攪拌3小時。將反應液減壓濃縮，所得反應混合物以D E A E -纖維素之離子交換柱層析精製，依次溶離以氯仿-甲醇（2 : 1 )及0· 0 5 m ο 1 / L乙酸銨（氯仿-甲醇-水（2 : 3 : 1 )溶液）。收集含目的物之部份於分液漏斗，加入0 · 5 mο 1 /L鹽酸水溶液以調至p Η 3。加入氯仿（1 〇mL )進行分層，收集氯仿層並減壓蒸除溶劑，可得標題化合物（95mg，產率73% )。 IR vmax (ΚΒι.) 3 340，3 2 8 8，3066，.3004，295 5，2924，2 8 5 3， 1656, 1 6 3 2 cm"1 · 1 Η - N M: R ( 5 0 0 Μ Η z , C D 3 〇 D + C D C 13 ) δ 0.8 9 ( 1 2 H，t，J 二 6.8 Hz), 1.2 8 -1.6 5 ( 7 4 H，m )，] · 7 5 ( 2 H , q · J 二 6.8 H z )，1.95-2.0 3 200413400 (6H，m)，2.26 (2H，t，J = 8.8-6.8 Hz)，3.26 - 3.3 0 (3 H，m)， 3.31 (3H，s)，3.41 (3H，s)，3.5 1- 3.76 (12H，m)，3.80-3.83 (2H? m), 4.02-4.09 (4H, m), 4.18 (1H, m), 4.58 (1H, d, J-7.8 Hz), 5.3 1-5.37 (2H, m). MS (ESI，陰性）m/z，1312 (M-Η)' HRMS (ESI，陰性），計算値 C68H132N〇I8P2: 1312.8916 ;實測値：1 3 1 2.8 9 0 6 . 〔實施例1 7〕 (6 —〇一{2 —去氧一3 —〇一[(R) — 3 —甲氧癸基]—6 一〇一甲基一2— [(Z) — 11—十八碳烯醯胺基]一 4一〇一膦酸基一 β — D —吡喃葡糖基}一 2，3—二一〇一十二基一 a — D —吡喃葡糖基）氫磷酸甲酯 (1) 2— (2’ 3— 一一〇一十二基一 4，6 —〇一亞異丙基一 α — D -吡喃葡糖基）呋喃（第F a 1工程及第F a 2(a)工程）將2— (2，3，4，6—四一〇一节基—α—D — □比喃蔔糖基）呋喃（Tetrahedron Lett .，34，7323— 7326 ( 1 99 3 )，已知化合物）（4.00g，6.77 mmol )溶在四氫呋喃 (40 m L) ’加入10% f巴—碳觸媒（203 mg)，於氫氣及室温下擾ίΦ 3小日^。灑除觸媒後’將爐液濃縮。所得殘濟溶在Ν，Ν —二甲基甲醯胺（丨4mL )，於冰冷却下加入2 — 甲氧丙烷（1 .OmL，10.4 mmol )及對甲苯磺酸一水合物（ 1 33mg, 0.699mm〇l )，於室温下攪拌2小時。將反應液減壓濃縮，以矽膠柱層析純化（己烷：乙酸乙酯，]:4 )， 185 - 200413400 可得油狀化合物。所得油狀物溶在N，N —二甲基甲醯胺（1 4 m L )，於冰冷却下加入氫化鈉（6 2 1 m g，5 5 %油性，1 4.2 m ο I )，攪拌2 0 分。加入1 —溴十二碳儲（2 · 7 5 m L , 1 1 . 5 m m ο 1 )，緩慢回温至5 〇 °C，於温度攪拌1小時。於0 °C下冷却，加入飽和氯化銨水溶液，以乙酸乙酯萃取3次，將有機層以水及飽和食鹽水依次洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，20 : 1 )，可得標題化合物 (1.79g，產率 44%)。 ]H-NMR ( 400 MHz, CDC13) δ 0.88 (6Η, t, J-6.6 Hz), 1.22-1·3 8 (3 6H，m)，1.526 (3H,s)，1.528 (3H，s)，1.5 6- 1.59 (4H， m)，3·37 (1H，dt, J二9.9，2.6 Hz)，3.47-3.82 (9H，ni)，5.14 (1H，d，J二6.4 Hz)，6.36 (1H，dd，J = 3,3，1.8 Hz)，6.52 (1H， d，J二3.3 Hz)，7.44 (1H，d，J=1.8 Hz). MS (FAB,陽性）m/z，605 (M + H) + . (2) (2，3 —二一〇一十二基一4，6 —〇一亞異丙基一 α 一 D —吡喃葡糖基）甲醇（第F a 2(b)工程，第F a 2(c)工程及第F a 3工程）將（1 )所得化合物（1 . 3 2 g，2 . 1 7 mmo1 )溶在四氯化碳一乙膳一水混合溶劑（2 : 2 : 3，3 5 m L ) ’加入過碘:酸納（ 2.97g, 13.9mm〇l)後，於冰冷却下加入氯化釕水合物（ 4 7.8 m g , 0.2 3 0 m m ο 1 )，攪拌2 · 5小時。加入1 0 %硫代硫酸鈉水溶液，以乙酸乙酯萃取3次。將有機層以水及飽和食鹽水依次洗浄，於硫酸鎂下乾燥’減壓蒸除溶劑。所得Extraction with ethyl acetate ', the organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, 95: 5) to obtain the title compound (3.40 g, yield 62%). IR vmax (CHCI3) 2927, 2855, 1 6 4 2 cm " 1!! H-NMR (500 MHz, CDCh) δ 0.88 (6H, t, J = 6.8 Hz), 1.26-1.56 (46H, m, including 3H, s, at 1.40, 3 H, s, 1.48 ppm), 2.39-2.50 (2H, m), 3.37 (1H, t, J = 8.8 Hz), 3.41-3.46 (2H, m), 3.49-3.56 (2H, m), 3.59-3.65 (3H , m), 3.71 (1H5 m), 3.81 (1H, dd, J = 4.9, 10.7 Hz), 4.06 (1H, m), 5.06-5.14 (2H, m), 5.78 (1H, m). MS (FAB (Positive) m / z, 619 (M + K) +, 603 (M + Na) +, 579 (ΜΗ) 'HRMS (ESI, positive), calculate 値 C 3 6 H 6 8 〇5 N a: 6 0 3.4 9 7 2; Measured gadolinium: 603.4953. (3) 2 — (2,3-dioxal-12-yl-4,6--0-isopropylidene-178-200413400 gyl-α-D-glucopyranose Glycosyl) ethanol (E a 3rd project) The compound obtained in (2) (3.25 g, 5.59 mmol) was dissolved in acetone (40 m L), water (10 m L) was added, and sodium periodate (3.5 2 g, 1 6.5 mm ο 1) and tungsten tetroxide (2 · 5% tertiary butanol-soluble Solution, 2.0 mL, 0.160 mmol), and stirred at room temperature for 2 hours. Added a saturated aqueous sodium thiosulfate solution, extracted 5 times with ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, the obtained residue was dissolved in ethanol (40 ml), and sodium borohydride (2.55 mg, 6.74 mm ο 1) was added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction solution A saturated ammonium chloride aqueous solution was added to stop the reaction, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: Ethyl acetate, 7: 3) to obtain the title compound (1.61 g, yield 49%). IR vmax (KBr) 3 522, 299 8, 29 54, 29 1 9, 285 1 cm " 1 · iH- NMR (500 MHz, CDC13) δ 0.88 (6H, t, J-6.8 Hz), 1.26-1.33 (36H, m), 1.40 (3H, s), 1.48 (3H, s), 1.52-1.58 (4H, m ), 1.93-1.97 (2H, m), 2.21 (lH, t, J = 5.9-4.9Hz, 0H), 3.38 (1H, t, J = 8.8 Hz), 3.42-3.49 (2H, m), 3.52 -3.57 (2H, m), 3.60-3.82 (7H, m), 4.20 (1H, m). MS (FAB, Positive) m / z, 623 (M + K) +, 607 (M + Na) +, 585 (M + H) +. HRMS (ESI, positive), calculated 値 C35H6806Na: 607.493 2; measured fit: 607.4 8 8 5. (4) (2,3-Di--12-dodecyl-1,4-6-isopropylidene-1-179-200413400 α-D-glucopyranosyl) ethyl phosphate diallyl Esters (E a 4th project) The compound (3) (530 mg, 0.9 0 6 mm ο 1) obtained in (3) was dissolved in tetrahydrofuran (5 ml), and 1 Η-tetra hydrazine (8 3 mg, 1. 18 mm ο 1) and bis (burned propoxy) (diisopropylamino) phosphine (25 Omg, 1.01 mmol), and stirred at room temperature for 2 hours under nitrogen. After cooling at 0 ° C, 30% aqueous hydrogen peroxide (0.5 mL) was added, and the mixture was stirred for 1 hour. A saturated aqueous sodium thiosulfate solution was added, followed by extraction with ethyl acetate three times. The organic layer was washed sequentially with saturated sodium bicarbonate and saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate, 7: 3) to obtain the title compound. (619 mg, yield 92%). IR vmax (CHC13) 2927, 2 8 5 5 cm'1 · ^ -NMR (400 MHz, CDC13) δ 0 · 8 8 (6 Η, t, J = 6.6-7 · 3 Η z), 1.22- 1.26 ( 3 6H, m), 1.39 (3H, s), 1.47 (3H, s), 1.51-1.54 (4H, m), 2.03 -2.08 (2H, m), 3.31-3.73 (9H, m), 3.81 (1H , dd, J = 5.1, 11.0 Hz), 4.08-4.20 (3H, m), 4.52-4.56 (4H, m), 5.19-5.39 (4H, m), 5.90-5.99 (2H, m). MS (FAB , Positive) m / z, 7 8 3 (M + K) +, 7 67 (M + Na) +, 745 (M + H) +. HRMS (ESI, positive), calculated 値 C41H77〇9Na: 767.5208; found Rhenium: 7 6 7 · 5 1 8 9 · (5) (2,3-2101012-α-D-glucopyranosyl) diallyl ethyl phosphate (E5 project ) The compound obtained in (4) (605 mg, 0.8 1 3 mm ο 1) was dissolved in 80% acetic acid aqueous solution (10 mL), and stirred at 60 ° C for 1 hour. The reaction solution was concentrated under reduced pressure, δδ-200413400, diluted with ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 1: 9) to obtain the title compound (4 62 mg, yield 81%). IR vmax (CHC13) 3 5 94, 3446, 2928, 285 6 cm · 1 · ^ -NMR (500 MHz, CDC13) δ 0 · 8 8 (6 H, t, J = 6.8 H z), 1.26- 1.3 1 (3 6H, m), 1.52- 1.5 8 (4H, m), 1.87 (1H, m), 2.06 (1H, m), 3.17 (1H, d, OH), 3.28 (1H, m), 3.44- 3.68 (8H, m, including 0H), 3.79 (1H, m), 3.98 (1H, m), 4.12 (1H, m), 4.18 φ (1H, m), 4.38 (1H, m), 4.54- 4.57 (4H, m), 5.25 -5.3 9 (4H, m), 5.91-5.98 (2H, m). MS (FAB, positive) m / z, 743 (M + K) +, 727 (M + Na) +, 705 (M + H) +. HRMS (ESI, positive), calculated 値 C38H7409P: 705.5070; found 値: 705.5072. (6) (6-〇一 {2-—desoxy-4—〇-diallyl phosphine Acid group—3—〇-[(R) —3-methoxydecyl] -6—〇-methyl-2 — [(2,2, · 2-trichloroethoxycarbonyl) amino] —β— D-glucopyranosyl group-2,3-2,120-yl-α -D-pyranylglucosyl) ethyl allyl phosphate (Eb 1 project) -4-0-diallylphosphonic acid group 3 10-{(R) -3-methoxydecyl} 6-〇-methyl- 2-(2, 2, 2, 3- Ethoxycarbonylamino) -D-glucopyranose (U.S. Patent No. 5 9 3 5 9 38, known compound) (560 in g, 0.8 0 1 mm ο 1) dissolved in dichloromethane (5 m L) -181-200413400, dichloroacetonitrile (0.4 m L, 3.99 mm ο 1) and carbon shavings (53 mg, 0.] 61 mmol) were added and stirred at room temperature for 1 hour. It was diluted with dichloromethane, washed with a saturated sodium bicarbonate aqueous solution and a saturated saline solution, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude imidate was dissolved in dichloromethane (5 mL), and the compound obtained in (5) (283 mg, 0.401 mmol) and a molecular sieve 4 A (420 mg) were added, and the mixture was stirred at room temperature for 30 minutes under nitrogen. The reaction solution was cooled at 0 ° C, and trifluoromethanesulfonate (5 pL, 0.028 mmol) was added, followed by stirring for 1 hour. A saturated aqueous sodium hydrogen carbonate solution was added to stop the reaction, and extraction was performed with dichloromethane. The organic layer was washed with water and saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate, 1: 4) to obtain the title compound (312 mg, 56% yield). IR vmax (CHC13) 3 2 6 8, 3 08 8, 2928, 28 5 6, 1 7 3 8 cm " 1 ·] H-NMR (500 MHz, CDC13) δ 0 · 8 8 (9 H, t, J = 6 · 8 H z), 1.14-1.79 (54H, m), 1.88 (1H, m), 1.98 (1H, m), 2.90 (1H, d, J = 2.9 Hz, 0H), 3.22-3.3 8 (7H, m, containing 3H, s, at 3.27 ppm), 3.39 (3H, s), 3.44-3.5 8 (5H, m), 3.63 (1H, dd, J = 4.9, 10.7 Hz), 3.69- 3.79 (7H, m), 3.97 (1H, d, J 2 11.7 Hz), 4.12-4.19 (2H, m), 4.28 (lH, q, J = 9.8, 8.8Hz), 4.35 (lH, m) , 4.52-4.60 (8H, m), 4.71 (1 H, d, J = 8.8 H z), 4.6 6, 4.8 2 (2 H, AB q, J = ll.7 Hz), 5.24-5.39 (8H, ni), 5.90-5.98 (4H, m), 7.17 (1H, d, J = 7.8 Hz, NH). MS (FAB, positive) m / z, 1 422 (M + K) +, 1406 (M + Na ) + · HRMS (ESI, positive), calculated 値 C65Hi18Cl3N019P2Na: 1406.6727; found 値: 1406.6704. 182 200413400 (7) (6 — 0 — {2 —deoxy-1 — 0 — 12 j: ciproflonic acid —3—〇 — [(R) — 3 —methoxydecyl] -6—〇-methyl-2 — [(Z) — 1 1 octadecylamino] —β—D — Mumble Glycosyl 丨 -2,3-di-12-dodecyl-1α-D-glucopyranosyl) diallyl phosphate (E2 project) The compound (6) obtained (290mg, 0.210 mmol) was dissolved in tetrahydrofuran (5 ml), zinc powder (270 mg, 4.13 mmol) and acetic acid (0.5 ml) were added, and the mixture was stirred at room temperature for 2 hours. The zinc powder was filtered off, and then concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, and dried over magnesium sulfate. Filtration, evaporation of the solvent under reduced pressure, the obtained crude amine was dissolved in dichloromethane (5 mL), (z)-1 1 octadecenoic acid (71 mg, 0.251 mmol) and 1-ethyl-3-(3 — Dimethylaminopropyl) carbodiimide hydrochloride (65mg, 0.341 mmol), and stirred at room temperature for 24 hours. The reaction solution was diluted with dichloromethane, washed with water and saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate, 1: 4) to obtain the title. Compound (158mg, yield 51%). Lu IR Vmax (CHC13) 3454, 3 3 1 0, 2928, 28 5 6, 1 6 64 cm'1 ·! H-NMR (500 MHz, CDCI3) δ 0.88 (12H, t, J 6.8 Hz), 1.26 -1.7 9 (7 6H, m), 1.90- 1.94 (2H, m), 2.00-2.01 (4H, m), 2.14-2.25 (2H, m), 3.06 (1H, d, J = 4.9 Hz, OH) , 3.25-3.40 (11H, m, including 3H, s, 3.28 ppm, 3 H, s, 3.38 ppm), 3.45-3.56 (3H, m)? 3.60- 3.6 3 (3 H, m), 3.67-3.7 7 (5 H, m), 3.98 (1H, t, J = 9.8 Hz), 4.0 j (1 H, d, J = 1 0.7 Hz), 4.11-4.21 (3 Η, πί), 4.25 -183-200413400 ( 1H, q, J = 7.8 Hz), 4.54-4.59 (8H, m), 4.99 (1H, d, J = 7.8 Hz), 5.23-5.3 8 (1 0H, m), 5.90-5.99 (4H, m) , 7.00 (1H, d, J = 7.8 Hz, NH). MS (FAB, positive) m / z5 1512 (M + K) +, 1 496 (M + Na) +. HRMS (ESI, positive), calculate 値C80H] 49N〇18P2Na: 1497.0126; Measured tritium: 1 497.008 1. (8) Monohydrogen phosphoric acid (6-〇一 {2-—desoxy-3—〇 — [(r) — 3—methoxydecyl] —2 — [(Z) — 1 1 —octadecenylamino] — 4 —0-phosphonic acid group — β — D —D glucosyl group — 2,3,210-dodecyl-1 α — D-glucopyranosyl) ethyl ester (Eb 3 project) The compound (145 mg, 0.098 mmol) obtained in (7) was dissolved in tetrahydrofuran (5 mL), and triphenylphosphine (13 mg, 0.051 mmol) was added. , Triethylamine (70 μl, 0.502 m mol), formic acid (38 μl, 1.0 mmol) and triphenylphosphine palladium (6 mg, 0.005 mmol), and stirred under nitrogen at 50 ° C for 3 hours. The reaction solution was concentrated under reduced pressure, and the obtained reaction mixture was purified by DEAE-cellulose ion-exchange column chromatography, followed by dissolution with chloroform-methanol (2: 1) and 0.5 · 5 m ο 1 / L ammonium acetate (chloroform-methanol). -Water (2: 3: 1) solution). Collect the part containing the target substance in a separatory funnel, and add 0 · 5 mο 1 / L aqueous hydrochloric acid solution to adjust to p Η 3. Chloroform (10 mL) was added for layer separation. The chloroform layer was collected and the solvent was distilled off under reduced pressure to obtain the title compound (95 mg, yield 73%). IR vmax (ΚΒι.) 3 340, 3 2 8 8, 3066, .3004, 295 5, 2924, 2 8 5 3, 1656, 1 6 3 2 cm " 1 · 1 Η-NM: R (5 0 0 Μ Η z, CD 3 〇D + CDC 13) δ 0.8 9 (1 2 H, t, J 2 6.8 Hz), 1.2 8 -1.6 5 (7 4 H, m),] · 7 5 (2 H, q · J 2 6.8 H z), 1.95-2.0 3 200413400 (6H, m), 2.26 (2H, t, J = 8.8-6.8 Hz), 3.26-3.3 0 (3 H, m), 3.31 (3H, s), 3.41 (3H, s), 3.5 1- 3.76 (12H, m), 3.80-3.83 (2H? M), 4.02-4.09 (4H, m), 4.18 (1H, m), 4.58 (1H, d, J- 7.8 Hz), 5.3 1-5.37 (2H, m). MS (ESI, negative) m / z, 1312 (M-Η) 'HRMS (ESI, negative), calculate 値 C68H132N0I8P2: 1312.8916; measured 实: 1 3 1 2.8 9 0 6. [Example 17] (6-〇一 {2-— deoxy-3—〇 — [(R) — 3-methoxydecyl] -6—10-methyl-1— [(Z) — 11-octadecenylamido]-4-10 monophosphonic acid group β-D-glucopyranosyl}-2,3-21010 dodecyl-a-D —Pyranylglucosyl) hydrogen methyl phosphate (1) 2— (2 ′ 3—11012 dodecyl-4,6—0—isopropylidene A-α-D-glucopyranosyl) furan (Fa 1 process and F a 2 (a) process) will be 2- (2,3,4,6-410-one group-α- D — □ thiopyranosyl furan (Tetrahedron Lett., 34, 7323-7326 (1 99 3), a known compound) (4.00 g, 6.77 mmol) was dissolved in tetrahydrofuran (40 ml), 10% f was added Bar—carbon catalyst (203 mg), disturbed for 3 hours at hydrogen and room temperature ^. After the catalyst is sprinkled, the furnace liquid is concentrated. The obtained residue was dissolved in N, N-dimethylformamide (4 mL), and 2-methoxypropane (1.0 mL, 10.4 mmol) and p-toluenesulfonic acid monohydrate (1 33 mg, 0.699) were added under ice cooling. mmOl), and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and purified by silica gel column chromatography (hexane: ethyl acetate,]: 4). 185-200413400 to obtain an oily compound. The obtained oil was dissolved in N, N-dimethylformamide (1 4 ml), and sodium hydride (6 2 1 mg, 55% oily, 14.2 m ο I) was added under ice cooling, and the mixture was stirred for 2 0 Minute. Add 1-bromododecane storage (2.75 m L, 1 1.5 m m ο 1), slowly return to 50 ° C, and stir at temperature for 1 hour. It was cooled at 0 ° C, a saturated ammonium chloride aqueous solution was added, and extraction was performed three times with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 20: 1) to obtain the title compound (1.79 g, yield 44%). ] H-NMR (400 MHz, CDC13) δ 0.88 (6Η, t, J-6.6 Hz), 1.22-1 · 3 8 (36H, m), 1.526 (3H, s), 1.528 (3H, s), 1.5 6- 1.59 (4H, m), 3.37 (1H, dt, J2 9.9, 2.6 Hz), 3.47-3.82 (9H, ni), 5.14 (1H, d, J2 6.4 Hz), 6.36 (1H , Dd, J = 3, 3, 1.8 Hz), 6.52 (1H, d, J = 3.3 Hz), 7.44 (1H, d, J = 1.8 Hz). MS (FAB, positive) m / z, 605 (M + H) +. (2) (2,3-dioxalyl-12,6-isopropylidene-α-D-glucopyranosyl) methanol (Fa 2 (b ) Project, F a 2 (c) and F a 3 Projects) The compound (1.32 g, 2. 17 mmo1) obtained in (1) was dissolved in a mixed solvent of carbon tetrachloride, ethyl acetate and water. (2: 2: 3,3 5 m L) 'After adding periodide: sodium acid (2.97 g, 13.9 mm), ruthenium chloride hydrate (4 7.8 mg, 0.2 3 0 mm) was added under ice cooling. ), Stirring for 2.5 hours. A 10% aqueous solution of sodium thiosulfate was added, and extracted three times with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Income

200413400 残渣溶在乙醚（3 5mL )，於冰冷却下加入三甲矽烷重氮甲院一己院溶液（8.23mL，10重量％，4.77mm〇1)，攪拌45 分。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，1 0 : 1 )，可得油狀化合物。所得化合物溶在乾燥四氫呋喃（1 〇 ni L )，於冰冷却下少里加入氣化錐銘（2 5 4 m g，6.6 9 m m ο 1 )，於冰冷却下擾伴1 小時後，加入乙酸乙酯。所得混合溶液以飽和氯化銨水溶液’水及飽和食鹽水依次洗浄，於硫酸鈉乾燥，減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，4 : 1 )，可得標題化合物（533mg, 0.934mmol)。 !H-NMR ( 400 MHz, CDC13) δ 0.88 (3H，t，J = 6.6 Hz)， 1.26- 1.3 2 (3 6H, m), 1.40 (3H, s), 1.48 (3H5 s), 1.53-1.56 (4H，m), 2.15 (1H，t，J = 5.7 Hz, OH), 3.40-3.74 (9H, m)， 3.85-3.89 (3H，m)，4.10-4.15 (1H，m). MS (FAB,陽性）m/z，59 3 (M + Na) +，57 1 (M + H) + . HRMS (ESI，陽性），計算値 C34H66〇6Na: 5 93.4757 ;實測値：593.4782. (3) (2，3 —二一〇一十二基一4，6 —〇一亞異丙基一α 一 D —毗喃葡糖基）甲磷酸二烯丙酯（第F a4工程）將（2 )所得化合物（5 3 3 m g , 〇 . 9 3 4 m m ο 1 )，依實施例1 6 (4 )之方法反應，可得標題化合物（65 3 mg，產率96% ) 〇 1 Η - N M R ( 4 0 0 MHz, C D C 13 ) δ 0.88 ( 6 H , t, 1 = 6.6 Hz), 1 . 2 2 - 1 . 2 6 ( 3 6 H，ni)，] . 3 9 ( 3 H，s)，1 . 4 7 ( 3 H，s)，1.4 8 - 1 . 5 8 200413400 (4H，m)，3.2 9 - 3.3 3 ( 1 H，m)，3.42- 3.72 (8H，m)，3.84-3.87 (1H，m)，4.21-4.28 (2H，m)，4.3 5 -4.40 ( 1 H，m)5 4.53-4.58 (4H，m)，5.25-5.40 (4H，m)，5.90-6.00 (2H，m)· MS (FAB,陽性）m/z，7 5 3 (M + Na) +，73 1 (M + H) + . (4) (2，3 —二一〇一十二基一a — D —批喃葡糖基）甲磷酸二烯丙酯（第F a 5工程）將（3 )所得化合物（6 1 7 m g , 0.8 4 4 m m ο 1 )，依實施例1 6 (5 )之方法反應，可得標題化合物（346mg，產率59% ) 〇 ^-NMR ( 500 MHz, CDC13) δ 0.8 8 ( 3 Η，t，J = 6.8 Η z )， 1.26- 1.29 (3 6Η，m)，1.53-1.61 (6Η，m)，3.02-3.03 ( 1 Η, m)， 3.42-3.70 (9H，m)，3.91-3.93 (2H，m)，4.17 (1H，dt, J=ll.7, 2.9 Hz), 4.29-4.31 (1H, m), 4.38-4.44 ( 1 H, m), 4.55-4.60 (4H, m), 5.25-5.40 (4H, m), 5.92-5.98 (2H, m). MS (FAB,陽性）m/z，713 (M + Na) +，691 (M + H) + . (5) (6 —〇一 {2 —去氧一 4 一〇一二烯丙膦酸基一3 —〇 —[(R) — 3 —甲氧癸基]—6 —〇一甲基一2— [(2，2，2 —三氯乙氧羰基）胺基]一 β - D —吡喃葡糖基丨—2，3 —二一〇一十二基一 a - D —吡喃葡糖基）甲磷酸二儲丙酯（第 F b 1工程）將（4 )所得化合物（2 80mg, 0.405mm〇l )，依實施例16 (6 )之方法反應，可得標題化合物（2 〇 6 m g ,產率3 7 % ) 〇 1R v m a X (ΪΙ 旲 J 3 2 8 4，3 0 8 4 , 2 9 2 6，2 8 5 6，1 7 4 9 , 1 6 5 0，1 5 4 5 c m _ 1 200413400 iH-NMR ( 500 MHz，CDC13) δ 0.88 (9H, t, J-6.8 Hz), 1.26-1.30 (42H，m)，1.40—1.61 (9H，m)，1.68-1.76 (2H，n〇， 3.09 ( 1 H, d，J = 6.8 Hz), 3.2 3 - 3.2 8 (4 H，m，含 3 H , s，a t 3.2 8 ppm), 3.35-3.66 (13H，m，含 3H，s，at 3.39 ppm)，3.73-3.79 (4H，m)，3.8 8 - 3.9 8 (3 H，m)，4.14-4.21 (2H，m)，4.27-4.39 (2H，m)，4.55-4.59 (8H，m)，4.70-4.81 (3H，m), 5.23-5.28 (4H，m)，5.35-5.40 (4 H，m)，5.90-5.99 (4H，m)，6.19 (1H， b r . s ). MS (FAB,陽性）m/z，1 3 92 (M + Na) + . HRMS (ESI，陽性），計算値 C64H116Cl3N〇19PNa: 1 3 92.65 82 ；實測値：1 392.6602. (6) (6 —〇一 {2 —去氧一4 一〇一二烯丙膦酸基一 3 一〇 —[(R) — 3 —甲氧癸基]—6 —〇一甲基一 2— [(Ζ) 一 11 一十八碳烯醯胺基]—β - D —吡喃葡糖基} — 2，3 -二一 ◦ 一十二基一 α—D —吡喃葡糖基）甲磷酸二烯丙酯（第Fb2 工程）將（5 )所得化合物（1 1 1 m g , 0.0 8 0 9 m m ο 1 ) ’依實施例 16 ( 7 )之方法反應，可得標題化合物（60.3 mg，產率51% ；° IR vmax (131 ) 3 3 07, 3 08 5, 2925, 2 85 5, 1 7 3 9, 1 65 8，1 6 3 6, 1 5 4 8 cm-1 * 1 Η - N M R ( 5 0 0 MHz, C D C 13 ) δ 0.88 (12H, t, 1 = 6.6 Hz), 1.2 8 - 1.7 6 ( 8 1 H，m )，1 · 9 9 - 2.0 1 ( 4 H，m )，2 . 1 7 - 2.2 4 ( 2 H，m )， -189 - 200413400 3.28-3.96 (20H，m，含 3H，s，at 3.28 ppm，3H，s, at 3.38 ppm), 4.13-4.39 (5H, m), 4.56 (8H, m), 5.03 (1H? d, J = 8.2 Hz), 5.23 -5.39 (8H, m), 5.90-5.99 (4H, m), 6.44 (1H, d, J = 7.4 Hz). MS (FAB,陽性）m/z，1 482 (M + Na) + . HRMS (ESI,陽性），計算値 C79H147N018P2Na: 1 482.999 1 •，實測値：1 1 4 8 2 · 9 9 9 1. (7) (6 —〇一{2 —去氧一3 —〇一[(R) — 3 —甲氧癸基]—6—〇一甲基一2— [ ( Z ) — 11—十八碳嫌酿胺基]—4 —〇一鱗酸基一β — D —[1 比喃葡糖基}一2，3—二一〇一十二基一 α-D —吡喃葡糖基）氫磷酸甲酯（第Fb3工程）將（6)所得化合物（60.3mg，0.0413mmol)，依實施例 16 ( 8 )之方法反應，可得標題化合物（39.4mg,產率73% )° IR vmax (KBr) 2955, 2924, 2854, 2345, 1 654，1631 cnT1 · 4 - NMR ( 400 MHz，CD30D + CDC13 ) δ 0 · 9 0 (1 2 H，t，J = 6 · 2 Hz), 1.1 5- 1.76 (78H, m), 2.01-2.04 (4H, m)? 2.23-2.32 (2H, m)，3.25-3.42 (8H，m，含 3H，s，at 3.29 ppm, 3H，s，at 3.39 ppm)，3.5 2-3.84 ( 1 2H，m)，3·98 (1H，d，J=10.3 Hz)，4.04-4.31 (5H, m), 4.62 (1H, d, J=10.3 Hz), 5.3 3 -5.3 5 (2H, m). MS (ESI，陰性）m/z，1 298 (M-H)-. HRMS (ESI，陰性），計算値 C67H13〇N018P2: 1 298.8754 ;實測値：1 298.876 1. 〔實施例1 8〕 -190 - 200413400 3 —膦酸氧丙基6 —〇一 {2 —去氧一3 — ◦ — [(R) — 3 — 甲氧癸基]一 6 —〇一甲基一2— [(Z) — 11一十八醯胺基] 一 4 —〇一膦酸基一β— D —吡喃葡糖基丨一2，3 —二一〇一十二基一 α— D -吡喃葡糖苷 (1) 3—羥丙基2，3 —二一〇一十二基一 4，6—〇一亞異丙基一 α- D -吡喃葡糖苷（第G a 1工程）將實施例13(2)所得烯丙基2，3—二一〇—十二基—4 ，6 —〇一亞異丙基一a — D —吡喃葡糖苷（3.30g， 5.5 3 mmol )溶在四氫呋喃（25 mL)，於冰冷却下加入9— φ 硼烷雙環[3· 3· 1]壬烷（9— Β Β Ν )之0· 5mol/L四氫呋喃溶液（28mL，14.0mmol )，於室温下攪拌1 8小時。將反應液於〇°C下冷却，加入3mol/L氫氧化鈉水溶液（50mL )，30%過氧化氫水（1 8mL )，於室温下攪拌3小時，以乙酸乙酯萃取3次，有機層以飽和氯化銨水溶液，飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷：乙酸乙酯，7 : 3)，可得標題化合物（ 3.03g，產率 89%)。籲 IR vmax (CHC13) 3 506，2927，2855 cm-1 · W-NMR ( 500 MHz，CDC13 ) δ 0.88 (6H, t, J = 6.8 Hz), 1.25- 1.94 (48H，m,含 3H，s，at 1.4 8 ppm，3 H，s，at 1.40 ppm)，2.88 (1H，t，J = 6.8，4.9 Hz, OH)，3.28 (1H，dd，J = 3.9， 7.8 Hz), 3.49-3.85 ( 1 2H, m), 3.96 (1H, m)? 4.87 (1H, d, J = 3.9 Hz). MS (FAB，陽性）m/z，65 3 (M + K)' 637 (M + Na) +，615 -191 - 200413400 (M + H) + . HRMS (ESI,陽性），計算値 C36H7〇07Na: 637.50 1 1 ;實測値：637.5034. (2) 3—（二烯丙膦酸氧基）丙基2，3—二一〇一十二基—α- D —吡喃葡糖苷（第G a2工程及第G a3工程）將（1 )所得化合物（9 8 1 m g，1 · 5 9 m m ο 1 )，依實施例1 6 (4)及（.5)之方法反應，可得標題化合物（ 828mg,產率 7 1 % )。 IR vmax (CHC13) 3 600, 3 393, 2927，285 5 cnT1 · · iH-NMR ( 500 MHz，CDC13 ) δ 0.8 8 ( 6 H，t，J = 6 · 8 Hz), 1.25 - 1.3 3 (3 6H，m)，1.53- 1.59 (4H，m)，1.71 (1H，brs，OH)， 1.97-2.09 (3H，m，含 OH)，3.26 (1H，dd，J = 3.9，9.8 Hz)， 3.43 (1H, t, J = 8.8 Hz), 3.51-3.75 (7H, m), 3.83-3.91 (3H, m), 4.13 (1H, m), 4.27 (1H, m), 4.53-4.57 (4H, m), 4.89 (1H, d, J = 3.9 Hz), 5.25-5.39 (4H, m), 5.90-5.98 (2H, m). MS (FAB，陽性）m/z，773 (M + K) +，757 (M + Na) + , 735 (M + H) + . 籲 HRMS (ESI，陽性），計算値 C39H7601()P: 735.5 1 75 ;實測値：735.5180. (3) 3—(二烯丙膦酸氧基）丙基6 —〇一{2 —去氧一 4 一〇一二烯丙膦酸基一3 —〇一[(R) — 3—甲氧癸基]—6 — 〇一甲基一 2 —（2’ 2’ 2 —二氣乙氧鑛月女基）一β — D 一口比喃葡糖基}一 2，3—二一 ◦一十二基_α— D —吡喃葡糖苷 (第G b 1工程） -192 - 200413400 使用（2)所得化合物（ 603mg, 0.821mmol)，依實施例 16 ( 6 )之方法反應，可得標題化合物（616mg,產率53% )° IR vmax (CHC13) 3450，3088，2928, 2873，2856，1 737 cm-1 · iH-NMR ( 500 MHz，CDC13 ) δ 0 · 8 8 (9 H，t，J = 6 · 8 H z), 1.25- 1.79 (54H, m), 1.95-2.06 (2H, m), 2.78 (1H, d, J = 2.9 Hz，OH)，3·24 (1H，dd，J = 3.9，9·8 Hz)，3.28 (3H，s), 3.30 (1H，m)，3.39 (3H，s)，3·41-3·86 (17H，m)，4.08 (1H，d， J = 8.8 Hz), 4.12-4.24 (2H，m)，4.29 (1H，q，J = 8.8, 9.8 Hz)， 4.52-4.60 (8H, m)，4.72，4·76 (2H，ABq，J = 11.7 Hz)，4·84 (1H，d，J = 3.9 Hz)，4·87 (1H，d，J = 7.8 Hz)，5.24-5.39 (8H， m), 5.90-5.98 (4H, m), 6.03 (1H, brs, NH). MS (FAB，陽性）m/z，1452 (M + K) +，1436 (M + Na) + . HRMS (ESI，陽性），計算値 C66H120Cl3N〇20P2Na·· 1436.6844 ；實測値：1436.6847. (4) 3—(二烯丙膦酸氧基）丙基6 —〇一{2 —去氧一4 — 〇一二烯丙膦酸基一 3_〇一 [(R) — 3 —甲氧癸基]—6 — 〇一甲基一2 — [(Z) — 11—十八碳烯醯胺基]—β— D — 卩比喃葡糖基}— 2，3— __•一〇—十_^基一a — D —口比喃葡糖苷（第G b 2工程）使用（3 )所得化合物（3 80mg, 0.269mmol)，依實施例 16 ( 7)之方法反應，可得標題化合物（217mg,產率54% )° IR vmax (CHC13) 3454，33 19，3089，2928，2856，1 665 cm·1 · -193 - 200413400 ^-NMR ( 500 MHz, CDC13) δ 0 · 8 8 ( 1 2 H，t，J = 6 · 8 H z)， 1.25- 1.80 (76H, m), 1.95-2.05 (6H, m), 2.14-2.27 (2H, m), 3.17 (1H，d，J = 3.9 Hz，〇H)，3.21-3.24 (2H，m)，3·28 (3H, s), 3.30 (1H, m), 3.38 (3H, s), 3.41-3.82 (15H, m), 3.94 (1H, t, J = 9.8，8.8 Hz)，4.07 (1H，d, J = 8.8 Hz)，4.1 1-4.20 (2H，m)，4.25 (1H，q, J = 8.8, 9.8 Hz), 4.52-4.58 (8H, m), 4.84 (1H, d，J = 3.9 Hz), 5.16 (1H, d, J = 7.8 Hz), 5.23-5.39 (10H, m), 5.90-5.98 (4H, m)? 6.36 (1H, d, J = 6.8 Hz, NH). MS (FAB,陽性）m/z，1 542 (M + K) +，1 526 (M + Na) + · HRMS (ESI，陽性），計算値 C81H15iN019P2Na: 1 527.026 1 ;實測値：1 5 2 7.0 2 7 7 . (5) 3—膦酸氧丙基6 —〇一丨2 —去氧一 3 —〇一[(R) —3 —甲氧癸基]—6 —〇一甲基一 2 — [(Z) — 11—十八醯胺基]一4一〇一鱗酸基一 β — D —吡喃葡糖基丨一 2，3_二 —〇一十二基_a_D —吡喃葡糖苷（第Gb3工程）使用（4 )所得化合物（2 0 0 m g , 0 · 1 3 3 m m ο 1 )，依實施例 16 ( 8)之方法反應，可得標題化合物（150mg,產率84% )° IR vmax (KBr) 3285，3228，3069，3004, 2955，2924，285 3， 2 3 18cm·1· ^-NMR ( 500 MHz, CD3OD + CDCI3) δ 0 · 8 9 (1 2 H，t，J = 6 · 8 Hz), 1.30- 1.67 (74H，m)，1.72- 1.75 (2H，m)，1.93 - 1.99 (2H， m), 2.01-2.04 (4H, m), 2.20-2.30 (2H, m), 3.17 (1H, dd, J = 3.9, 9.8 Hz), 3.29 (3H, s), 3.33 (1 H，m)，3 · 3 9 (3 H，s)， -194 - 200413400 3.44 (1H, t, J = 9.8, 8.8 Hz), 3.48-3.67 (10H, m)? 3.73-3.85 (6H，m)，4.04-4.12 (4H, m), 4.48 (1H, d, J = 8.8 Hz), 4.85 (1H, d，J = 2.9 Hz)，5.31-5.38 (2H, m). MS (ESI,陰性）m/z，1342 (M-H)·. HRMS (ESI，陰性），計算値 C69H134N019P2: 1342.903 1 ;實測値 * 1342.9047. 〔實施例1 9〕 2 —膦酸乙基6 —〇一{2 —去氧一3 —〇一 [(R) — 3—甲氧癸基]—6 —〇一甲基一2— [(Z) — 11 —十八醯胺基]—4 —〇一膦酸基一β— D —吡喃葡糖基丨一2，3 —〇一二一十二基—β— D -吡喃葡糖苷 (1)烯丙基4，6 —〇一亞異丙基一 β— D —吡喃葡糖苷 (第A c 3工程）使用烯丙基2，3，4，6 —〇一四乙醯基一β— D —吡喃葡糖苷（Carbohydr.Res.，203，34 1 - 342 ( 1 99 1 ) ，已知化合物）（8.00g，20.6mm〇l )，依實施例16 ( 1 ) 之方法反應，可得標題化合物（4.52g，產率84%)。 IR vmax (KBr) 3493，3285, 3082, 2993, 292 1, 2882 cm'1 · ^-NMR ( 500 MHz, CDC13) δ 1 · 44 ( 3 H，s)，1 · 5 1 ( 3 H , s)， 2.82 (1H, d, J = 2.9 Hz, OH), 2.94 (1H, d, J = 2.0 Hz, OH), 3.27 (1H，td，J = 5.9，9.8 Hz)，3·48 (1H，m)，3·59 (1H，t， J = 8.8, 9.8 Hz), 3.65 (1H, m), 3.80 (1H, t, J = 9.8, 10.7 Hz), 3.93 (1H，dd，J = 5.9，10.7 Hz), 4.13 (1H，dd，J = 5.9, 12.7 Hz), 4.36 (1H, dd, J = 5.9, 12.7 Hz), 4.40 (1H? d，J = 7.8 Hz)， -195 - 200413400 5.22-5.34 (2H, m), 5.93 (1H, m). MS (FAB，陽性）m/z, 299 (M + K) +，28 3 (M + Na) +，261 (M + H) + . HRMS (ESI，陽性），計算値 C12H2G06Na: 283.1 169 ;實測値：2 8 3 · 1 1 5 3 . (2) 烯丙基2，3—二一〇一十二基一4，6 —〇一亞異丙基一 β— D -吡喃葡糖苷（第A C2工程）使用（1 )所得化合物（4.25g, 16.3mm〇l )，依實施例 16 ( 2)之方法反應，可得標題化合物（5.33g,產率55% )° 11^^((：11(：13) 2927，2855 請-1· ^-NMR ( 500 MHz, CDC13) δ 0 · 8 8 (6 Η，t，J = 6 · 9 Η z)， 1.26- 1.3 3 (3 6Η, m), 1.40 (3H, s), 1.47 (3H, s), 1.52-1.59 (4H, m), 3.12 (1H, t, J = 7.8, 8.0 Hz), 3.16 ( 1H, td, J = 4.9, 9.8 Hz), 3.62-3.68 (2H, m), 3.71-3.82 (3H, m), 3.90 (1H, dd, J = 4.9，10.7 Hz), 4.11 (1H, dd，J = 5.9，12.7 Hz)，4.34 (1H，dd, J = 5.9, 12.7 Hz), 4.37 (1H, d, J = 7.8 Hz), 5.18-5.34 (2H，m)，5.90 (1H，m). MS (FAB,陽性）m/z，635 (M + K) +，619 (M + Na) +，595 (Μη)' HRMS (ESI，陽性），計算値 C36H6806Na: 619.4911 ;實測値：619.4919. (3) 2_羥乙基2，3—二一〇一十二基一4，6— ◦一亞異丙基一 β— D —吡喃葡糖苷（第Abl工程） -196 - 200413400 使用（2)所得化合物（3.8 1g, 6.3 8mmol)，依實施例 1 6 ( 3 )之方法反應，可得標題化合物（3 · 2 5 g ,產率8 5 % )0 IR vmax (KBr) 3484, 2996，2919，285 1 cm·1 · j-NMR ( 500 MHz, CDC13 ) δ 0 · 8 8 (6 H，t，J = 6 · 8 H z)， 1.26- 1.3 3 (3 6H, m), 1.40 (3H, s), 1.48 (3H, s), 1.52-1.60 (4H, m), 2.72 (1H, t, J = 5.9-6.8 Hz, OH), 3.14 (1H, t, J = 7.8, 8.8 Hz), 3.20 (1H, td, J = 9.8, 4.9 Hz), 3.29 (1H, t, J = 8.8, 9.8 Hz), 3.55 (1H, t, J = 9.8 Hz), 3.62 (1H, m), 3.71-3.78 (6H, m), 3.80-3.92 (3H, m), 4.40 (1H, d, J = 7.8 Hz). MS (FAB,陽性）m/z，639 (M + K) + , 623 (M + Na)' 601 (M + H) + . HRMS (ESI,陽性），計算値 C35H6807Na: 623.4859 ;實測値：623.4869. (4) 2 —溴乙基2，3 —二一〇一十二基一4，6—〇一亞異丙基一 β— D -吡喃葡糖苷（第D a 1工程）將（3 )所得化合物（1.95 g, 3.25 mmol )溶在二氯甲烷（ 15mL )，加入四溴化碳（1.40g，4.22mm〇l )及三苯膦（ 1.29g, 4.92mmol )，於室温下攪拌1小時。將反應液以二氯甲烷稀釋，水，飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（己烷··乙酸乙酯，9 : 1 )，可得標題化合物（2.01 g,產率93%)。 IR vmax (CHC13) 2927, 2855 cm'1 · 4-NMR ( 500 MHz，CDC13 ) δ 0 · 8 8 (6Η，t，J = 6 · 8 Ηz)， -197 - 200413400 1.26- 1.34 (36H，m), 1.40 (3H, s)，1.47 (3H, s), 1.52-1.59 (4H, m), 3.10 (1H, t, J = 7.8, 8.8 Hz), 3.17 (1H, td, J = 4.9, 9.8 Hz), 3.26 (1H, t, J = 8.8 Hz), 3.48 (2H, t, J = 6.8 Hz), 3.54 (1H, t, J = 8.8, 9.8 Hz), 3.61-3.66 (2H, m), 3.71-3.76 (2H, m), 3.81-3.90 (3H, m), 4.13 (1H? m), 4.37 (1H, d, J = 6.8 Hz). MS (FAB,陽性）m/z，685 (M + Na) +，66 1 (M-H) + . HRMS (ESI,陽性），計算値 C35H67Br06Na: 685.4030 ;實測値：685.3994· (5) 2—(二烯丙膦酸基）乙基2，3 —二一〇一十二基一 β 一 D —吡喃葡糖苷（第D a2工程及第D a3工程）將（4)所得化合物（1.78g，2.68mm〇l)加入亞磷酸三烯丙酯（10mL)，於氮氣及180°C下加熱攪拌2小時，減壓濃縮，以矽膠柱層析純化（己烷：乙酸乙酯，2 : 3)可得混合物（2.28g)。將混合物溶在80%乙酸水溶液（15mL )，於60°C攪拌2小時，減壓濃縮，以乙酸乙酯稀釋。以水，飽和碳酸氫鈉水溶液及飽和食鹽水洗浄，於硫酸鎂下乾燥。減壓蒸除溶劑，以矽膠柱層析純化（乙酸乙酯：乙醇，20 : 1 )，可得標題化合物（834mg，產率44% )。 IR vmax (膜）33 94, 3085, 2925, 2855 cnT1 · 】H-NMR ( 500 MHz, CDC13 ) δ Ο · 8 8 (6 Η，t，J = 6 · 9 Η z)， 1.26- 1.3 1 (36Η, m), 1.51-1.61 (4H, m), 1.71 (1H, brs, OH), 2.21 (2H, dt, J = 7.8, 19.5 Hz), 2.57 (1H, brs, OH), 3.06 (1H, t, J = 7.8, 8.8 Hz), 3.19 (1H, t, J = 8.8, 9.8 Hz), 3.45 -198 - 200413400 (1H, m), 3.55 (1H, m), 3.63 (1H, m), 3.71-3.91 (5H, m), 4.10 (1H? m), 4.3 3 (1H，d, J = 6.8 Hz), 4 · 5 2 - 4.5 6 (4H，m), 5.24-5.3 8 (4H, m), 5.91-5.97 (2H, m). MS (FAB,陽性）m/z，743 (M + K) +，727 (M + Na) + . HRMS (ESI，陽性），計算値 C38H73 09PNa: 727.4 8 80 ;實測値：727.4916. (6) 2—（二烯丙膦酸基）乙基6 —〇一{2 —去氧一4一〇 —二烯丙膦酸基一 3_〇一 [(R) — 3 —甲氧癸基]—6 —〇 —甲基—2— [(2，2，2 —三氯乙氧羰基）胺基]—β— D — 吡喃葡糖基}— 2，3—二一〇_十二基一 β— D —吡喃葡糖苷（第D b 1工程）使用（5 )所得化合物（390mg, O.541mmol )，依實施例 16 ( 6)之方法反應，可得標題化合物（48 6mg，產率64% )° IR vmax (CHC13) 3257，308 8，2928，287 3，2856，1740 cm-1 · W-NMR ( 500 MHz, CDC13 ) δ 0 · 8 8 (9 H，t，J = 6 · 8 H z)， 1.26- 1.78 (54H, m), 2.16 - 2·27 (2H，m)，2·48 (1H，s, OH), 3.01 (1H, t5 J = 7.8, 8.8 Hz), 3.12 J = 8.8 Hz), 3.23- 3·29 (5H，m，含 3H，s, at 3.27 ppm)，3.36-3.41 (4H，m，含 3H, s, at 3.40 ppm), 3.45 -3.56 (3 H, m), 3.60-3.70 (3H, m), 3.74-3.91 (7H, m), 4.14-4.16 (2H, m), 4.23 (1H, d, J = 6.8 Hz), 4.28 (1H, q, J = 9.8 Hz), 4.51-4.60 (8H, m), 4.63 (1H, ABq, J=11.7 Hz), 4.74 (1H, d, J = 7.8 Hz), 4.86 (1H? ABq, J=1 1.7 Hz), 5.24-5.3 9 (8H, m), 5.89-5.98 (4H, m), 7.00 -199 - 200413400 (1 H, brs，NH). MS (FAB,陽性）m/z，1 422 (M + K) + , 1 406 (M + Na) + , 1384 (M + H) + . HRMS (ESI,陽性），計算値 C65H118Cl3N019P2Na: 1406.6747 ；實測値：1406.6772. (7) 2—(二烯丙膦酸基）乙基6 —〇一{2 —去氧一4 —〇 —二烯丙膦酸基一 3 —〇一 [(R) — 3 —甲氧癸基]—6 —〇 —甲基—2 — [(Z) — 11 一十八碳烯醯胺基]一 β— D —吡喃葡糖基}— 2，3—二一〇一十二基一 β— D —吡喃葡糖苷 (第D b 2工程）使用（6 )所得化合物（429mg，0.309mmol )，依實施例 16 ( 7)之方法反應，可得標題化合物（203 mg，產率45% )° IR vmax (CHC13) 3452, 3302, 3088, 2928, 2856, 1 664 cm'1 · ^-NMR ( 500 MHz, CDC13) δ 0.88 (12H, t, J = 6.8 Hz), 1.25 - 1.78 (76H, m), 1.99-2.01 (4H, m), 2.14-2.32 (4H, m), 3.02 (1H, t, J = 7.8, 8.8 Hz), 3.08 (1H? d, J = 3.9 Hz, OH), 3·14 (1H，t, J = 7.8, 8·8 Hz)，3·22-3.33 (5H, m，含 3H，s，at 3.28 ppm), 3.36 (1H, m), 3.38 (3H, s), 3.52-3.5 8 (2H, m), 3.60-3.86 ( 1 0H, m), 3.93 (1H, t, J = 8.8, 9.8 Hz), 4.03 (1H, m), 4.10 (1H, d, J = 9.8 Hz), 4.23 (1 H，d，J = 7 · 8 H z)，4 · 2 6 (1H, q, J = 9.8 Hz), 4.51-4.61 (8H，m)，5.13 (1H, d, J = 8.8 Hz)，5.23-5.3 8 ( 1 0H，m), 5.90-5.97 (4H，m)，6·65 (1H，m， NH). -200 - 200413400 MS (FAB,陽性）m/z，1512 (Μ + Κ) +，1 496 (M + Na) + · HRMS (ESI，陽性），計算値 C8〇H149N018P2Na: 1497.01 27 ;實測値：1497.0092. (8) 2_膦酸乙基6 —〇一{2—去氧一 3 —〇一[(R) — 3 —甲氧癸基]—6 —〇一甲基一2 — [(Z) — 11—十八醯胺基]—4 一〇一膦酸基一 β— D —吡喃葡糖基}一2，3—二— 〇一十二基一 β— D —毗喃葡糖苷（第Db3工程）使用（7 )所得化合物（1 8 8 m g，0 · 1 2 8 m m ο 1 )，依實施例 16 ( 8)之方法反應，可得標題化合物（14 lmg，產率84% )0 IR vmax (KBr) 3413，3287，307 1，3005，2955, 2924，2853， 2345， 1630CDT1· ]H-NMR ( 500 MHz, CD3OD + CDCI3) δ 0 · 9 0 (1 2H，t，J 二 6.8 Hz), 1.29-1.65 (74H, m), 1.73- 1.77 (2H, m), 2.01-2.03 (4H, m), 2.12-2.18 (2H, m), 2.25 (2H, t, J = 7.8 Hz), 2.99 (1H, t, J = 7.8, 8.8 Hz), 3.15 (1 H，t，J 二 8 · 8 H z)，3 · 2 9 - 3 · 3 7 (4 H，m，含 3H, s, at 3.31 ppm), 3.41 (3H，s)，3 · 5 7 - 3.8 7 ( 1 5 H，m)， 4.03-4.12 (3H, m), 4.28 (1H, d, J = 6.8 Hz), 4.62 (1H, d, J = 7.8 Hz)，5.3 1-5.37 (2H, m). MS (ESI，陰性）m/z，1312 (M-H)·. HRMS (ESI，陰性），計算値 C68H132N018P2: 1 3 1 2.8923 ;實測値：1 3 1 2.8 9 3 1 . 〔實施例20〕 2—（膦酸氧基）乙基3 — 0_癸基—6—0— {2 —去氧一 3 -201 - 200413400 —Ο—〔（R) — 3 —甲氧癸基〕一6— Ο —甲基一 2—〔 ( Ζ )一 11 一（十八碳燦酿基）胺基〕—4— 0-鱗酸基一 β - D 一啦喃葡糖基}— 2— 0一（3—氧基十四院醯基）—a— D — 吡喃葡糖苷 (1) 2 —羥乙基3 — 0 —癸基一4，6—0 —亞異丙基—α — D —吡喃葡糖苷（第H a 1工程）將實施例1 (3)所得烯丙基3 - 0 —癸基一 4，6— 0—亞異丙基一a— D —吡喃葡糖苷（2.20g，5.491 mmol)溶於乙腈—四氯化碳一水（2:2:3, 280mL)，加入過碘酸鈉（30g， 0.140 mol)及觸媒量氧化釕（lOOmg，0.751mmol)，劇烈攪拌1.5小時。將反應液減壓濃縮，以乙酸乙酯稀釋，以水及飽和食鹽水洗，於硫酸鎂下乾燥，過濾濃縮。溶於 DMF ( 5 OmL )，力口入三乙胺（2.00g，19.762mmol)及溴化烯丙基（2.45g, 20.25 1 mm〇l )，於5 0 °C攪拌1 · 5小時。反應物以乙酸乙酯稀釋，以稀鹽酸，水及重碳酸鈉溶液洗，於硫酸鎂下乾燥。過濾濃縮，以矽膠柱層析純化。溶離以環己烷一乙酸乙酯（3 : 1，再以1 : 1 )，可得烯丙酯，內酮及醛混合物1.734g。將混合物溶於乙醇（25mL)，加入硼氫化鈉（3 0 0 m g，7.9 3 m m ο 1 )，於室温下攪拌3小時。以乙酸將残留硼氫化鈉分解，以乙酸乙酯稀釋。以稀鹽酸，水及重碳酸鈉溶液洗，於硫酸鎂下乾燥。過濾濃縮，以矽膠柱層析純化。溶離以環己烷一乙酸乙酯（3 : 1 )，可得標題化合物（1. 1 9 7 g，產率5 4 % )。 IR vmax (II) 3 396 (br), 2994, 2926, 2856 cm*1. -202 - 200413400 400 MHz lH NMR (CDC13) δ 0.88 (3H, t, J = 6.8 Hz), 1.26 (14H，bs), 1·41 (3H，s)，1.49 (3H，s)，1.54- 1.59 (2H，m), 2.75 (1H, d, J = 5.9 Hz, OH), 2.90 (1H, bs, OH), 3.50-3.86 (12H, m), 4.93 (1 H，d，J = 3 · 7 Hz). FABMS (陽離子）m/z，405 [M + H] +，427 [M + Na] + . (2) 2 —（二烯丙膦酸氧基）乙基3 — O —癸基—4，6— O 一亞異丙基一 α—D-吡喃葡糖苷（第H a 2工程）將（1 )所得化合物（393mg，0.972mmol )溶在二氯甲烷 (1 OmL )，力口入 1H-四哇（102mg，1.457mmol，1.5 當量）及二異丙胺基磷酸二烯丙酯（262mg，1.069mm〇l，1·1當量 )，於室温下攪拌20分。加入四氫呋喃（10mL)，再加入30%過氧化氫水（20〇11^)，於室温攪拌15分。反應液以乙酸乙酯稀釋，以1 〇%硫代硫酸鈉水，重碳酸鈉溶液及食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，以矽膠柱層析純化。溶離以環己烷一乙酸乙酯（3 : 1 )，可得標題化合物（440mg，產率 80%)。 IR vmax (膜）3409 (br)，2994, 2926, 2857 cnT1· 400 MHz lU NMR (CDC13) δ 0.88 (3H, t, J = 6.6 Hz), 1.26 (14H, bs), 1.40 (3H, s), 1.49 (3H, s), 1.55- 1.59 (2H, m), 3.09 (1H, d, J = 8.1 Hz, OH), 3.44-3.94 ( 1 0H, m), 4.23-4.28 (2H, m), 4.55-4.60 (4H, m), 4.88 (1H, d, J = 3.7 Hz), 5.25-5.30 (2H, m), 5.36-5.43 (2H, m), 5.91-6.02 (2H, m). (3) 2 —（二烯丙膦酸氧基）乙基3— O —癸基—4，6— O 一亞異丙基一 2— Ο— (3-氧基十四烷醯基）—cx — D-吡 -203 - 200413400 喃葡糖苷（第H a3工程）將（2)所得化合物（ 440mg，0.779mmol)溶在二氯甲院 (3 OmL )，加入 3 —氧基十四院酸（ 280 mg, 0.858 mmol) 及1—乙基一 3— (3—二甲胺丙基）一碳化二亞胺鹽酸鹽 (179mg，0.935 mmol )，於室温攪拌4 0分後濃縮，以乙酸乙酯稀釋。以重碳酸鈉溶液及食鹽水洗浄，於硫酸鎂下乾燥。過濾濃縮，以矽膠柱層析純化。溶離以環己烷-乙酸乙酯（1 : 1 )，可得標題化合物（464mg，產率75% )。 IR vmax (膜）2926，2856，1 750，1719，1 650 (w)，1 627 (w) · cm'1. 400 MHz lU NMR (CDC13) δ 0.88 (3H, t? J = 6.8 Hz), 1.26 (22H, bs)，1.39 (3H，s)，1.40- 1.63 (9H, m，含 3H，s，at δ 1.49 ppm), 2.53 (2H, t, J = 7.3 Hz), 3.40-3.54 (3H, m), 3.61-3.75 (6H, m), 3.82-3.88 (2H, m), 4.19-4.23 (2H, m), 4.56-4.59 (4H, m), 4.77 (1H, dd, J = 3.7, 9.5 Hz), 5.03 (1H, d, J = 4.4 Hz), 5.26-5.41 (4H, m), 5.93-6.00 (2H, m). FABMS (陽離子）m/z，789 [M + H] +，81 1 [M + Na] + . # HRFABMS，C41H73012PNa 計算値：811.4737。實測値： 8 1 1.4724. (4) 2—(二烯丙膦酸氧基）乙基3— O —癸基一 2—0 —（ 3—氧基十四烷醯基）一 α— D—吡喃葡糖苷（第A b3工程 ) 將（3 )所得化合物（460mg，O.5 8 3 mmol )溶在80%乙酸水（46mL)，於85°C攪拌1.5小時。反應終了後，將反應 -204 - 200413400 液濃縮，以矽膠柱層析純化。溶離以甲醇一乙酸乙酯（1 : 19)，可得標題化合物（3 7 4 m g，產率8 6 % )，油狀化合物〇 IR vmax (膜）3407 (br)，2925，2855，1 747，1718，1 650 (w)， 14 6 5 cm'1. 400 MHz !H NMR (CDC13) δ 0.88 (3H, t, J = 6.6 Hz), 1.26 (30H，bs)，1·53·1.60 (4H，m)，2.51 -2·55 (3H，m,含 OH)， 2·66 (1H，d，J = 2.9 Hz, OH)，3.46-3.90 ( 1 1H，m，含 2H，s, at δ 3.50 ppm), 4.20-4.25 (2H, m), 4.55-4.59 (4H, m), 4.72 (1H, dd, J = 3.7, 9.5 Hz), 5.08 (1H, d, J = 3.7 Hz), 5.26-5.41 (4H? m), 5.91-5.99 (2H, m). FABMS (陽離子）m/z，749 [M + H] +，771 [M + Na] + · HRFABMS，C38H69012PNa 計算値：77 1.4425。實測値： 77 1.44 1 8. (5)2 —( 一細丙麟酸氧基）乙基3 — Ο —癸基—6 — Ο — { 2 一去氧一4—0 —二烯丙膦酸基一 3 — Ο—〔（R) — 3 —甲氧癸基〕一 6— 0 —甲基一 2-〔（2，2，2 —三氯乙氧鑛基）胺基〕一 β - D_[I比喃葡糖基}— 2—0—（3 -氧基十四院醯基）一（X— D—吡喃葡糖苷（第Cbl工程）使用（4)所得化合物（374mg，0.49 9mmol)及實施例1 (10)所用相同亞胺酸酯（ 422mg，0.4 99mmol)，依實施例1 ( 10)之方法反應，可得標題化合物（486mg，產率 6 8%)。 IR vmax (膜）3292 (br)，308 5 (w)，2927，2856，1 748，1721， -205 - 200413400 1 650 (w)，1 545，1460 cm"J . 400 MHz ]H NMR (CDC13) δ 0.88 (9H, t, J = 6.6 Hz), 1.26 (42H，bs)，1.40- 1.80 (8H, m)，2.52 (2H，t，J = 7.7 Hz)，2.80 (1H，bs，OH)，3.24-3.84 (24H, m，含 2 個 3H，s，at δ 3.29 and 3.39 p p m)，4 · 0 9 - 4.3 2 (4 H，m), 4 · 5 3 - 4 · 5 9 ( 8 H，m)，4 · 6 9-4.7 1 (3H，m)，4.87 (1H, m), 5.03 (1H，d，J = 3.7 Hz), 5.24-5.41 (8H，m)，5.90-5.99 (4H，m)，6·62 (4H，m)，6·36 (1H， bs, NH)· FABMS (陽離子）m/z，1450 [M + Na，35C1] +，1 45 2. HRFABMS C65H114Cl3N022P2Na 計算値：1450.6298。實測値：1450.6301 . (6) 2 —（二烯丙膦酸氧基）乙基3— O—癸基一6— O — {2 一去氧—4 一 0 — 一嫌丙鱗酸基一 3 — 0—〔（R) — 3-甲氧癸基〕一 6 — Ο —甲基—2—〔（Ζ) — 11-（十八碳嫌酸基 )胺基〕一 β— D —吡喃葡糖基}一 2 - 0 -（3 —氧基十四烷醯基）一 α-D —吡喃葡糖苷（第Cb2工程）使用（5 )所得化合物（477mg, 0.334mmol )，依實施例 1(11)之方法反應，可得油狀標題化合物（412mg，產率 81% )。 IR vmax (膜）3302，3086 (w)，2926，2855，1746，1719，1 654, 1 55 3，1 465 cm·1· 400 MHz !H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (60H, bs), 1.40- 1.80 ( 10H, m), 1.99-2.02 (4H, m), 2.17-2·27 (2H，m)，2.52 (2H，m), 3.20-3.9 1 (26H，m，含 2 個 3H， 200413400 s, at δ 3.29 and 3.38 ppm), 4.07-4.27 (6H? m), 4.54-4.57 (8H, m), 4.70 (1H, dd, J = 3.7, 9.5 Hz), 5.02 (1H, d, J = 3.7 Hz), 5.19 (1H, d, J = 8.1 Hz), 5.23-5.40 ( 1 0H, m)? 5.88-5.99 (4H，m), 6.51 (1H, d, J = 6.6 Hz，NH). FABMS (陽離子）m/z，1518 [M + H] +，1 540 [M + Na] + · HRFABMSC8〇HM5N〇2iP2Na 計算値：1540.9682。實測値： 1540.9653. (7) 2—（膦酸氧基）乙基3 — O —癸基—6 — Ο— {2 —去氧一3— 0—〔（R) — 3—甲氧癸基〕—6— 0 -甲基一2— · 〔（Ζ ) — 11—（十八碳燃醯基）胺基〕一 4— Ο —鱗酸基一 β— D —卩比喃葡糖基}一 2— Ο -（3-氧基十四院醢基）— α— D—吡喃葡糖苷（第Cb3工程）使用（6 )所得化合物（200mg，0.132mmol )，依實施例 1 ( 14)之方法反應，可得粉狀標題化合物（150mg，產率 8 4%) 〇 IR vmax (KBr) 3286 (br), 2925, 2854, 1742，1716，1 629， 1 552, 1 466 cm'1. · 400 MHz lH NMR (CDCI3-CD3OD, 5:1) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (60H, bs), 1.40- 1.63 (8H, m), 1.72-1.77 (2H, m), 1.99-2.04 (4H, m), 2.18-2.22 (2H, m), 2.53-2.57 (2H，m)，3.30-3.83 (24H，m，含 2 個 3 Η，s，at δ 3 · 3 0 an d 3.41 ppm), 4.01-4.14 (4H, m), 4.65-4.72 (2H, m), 4.98 (1H? d, J = 3.7 Hz), 5.30-5.36 (2H? m). FABMS (陰離子）m/z，1 3 56 [M-H]·. -207 - 200413400 HRFABMS C80H145NO21P2Na 計算値：1 540.9682。實測値： 1540.9653. C68H129N021P2 分析計算値：C，60.11; H，9.57; Ν，1·03; P， 4.56。實測値：C，59.83; Η，9.75; N，1.21; P, 4.38. 〔實施例2 1〕膦酸基3— O —癸基—6 - Ο — {2-去氧—3 — Ο—〔（R) —3—甲氧癸基〕一6— Ο—甲基一2—〔（Z) — 11—（十八碳烯醯基）胺基〕一 4一 0-膦酸基一 β - D—吡喃葡糖基 }一 2— 0— (3—氧基十四院醯基）一 α— D—批喃葡糖昔 (1)烯丙基3— Ο —癸基—4，6—0 —亞異丙基一 2— 0 一（3—氧基十四烷醯基）一 β— D —吡喃葡糖苷（第A a4 工程）將實施例1 ( 3 )所得烯丙基3 - 0 —癸基—4，6 — Ο -亞異丙基—β— D —吡喃葡糖苷（401mg，l.OOmmol)溶在二氯甲烷（4mL)，加入三乙胺（150mg，1.48mmol )及3—氧基十四院醯氯（313mg，1.20mmol)之二氯甲院（2mL)溶液，於室温下反應2小時後，以二氯甲烷稀釋。將二氯甲烷溶液以重碳酸鈉溶液洗及飽和食鹽水洗，於硫酸鎂下乾燥後過濾。將濾液減壓濃縮，以矽膠柱層析純化。溶離以環己烷一乙酸乙酯（6 : 1 )，可得標題化合物（400mg，產率6 4 % )。 IR vmax (膜）2923，285 3，1 752，1722，1 636，1 5 68 cnT1· 400 MHz !H NMR (CDC13) δ 0.88 (6H? t, J = 6.6 Hz), 1.26 (30H，bs)，1.40 (3H，s)，1.4 卜 1.68 (7H，m，含 3H，s，at δ 200413400 1.49 ppm)，2·56 (2H，t，J = 6.3 Hz)，3.23 (1H，m)，3.38-3.50 (4 H , m，含 2 H, s，a t δ 3 · 4 1 p p m)，3 · 6 6 - 3 · 8 2 ( 3 H，m), 3 · 9 2 (1H，m)，4·05 (1H, m)，4.30 (1H，m)，4.47 (1H，d，J = 8.1 Hz)，4_95 (1H，m)，5.14-5.27 (2H，m)，5.84 (1H，m)· FABMS (陽離子）m/z，623 [M_H] +，647 [M + Na] + · (2) 烯丙基3— O —癸基一 2 - O— (3—氧基十四烷醯基 )一 β— D —吡喃葡糖苷（第A a5工程）將（1)所得化合物（2.37g, 3.79mmol)，依實施例1 ( 5 )之方法反應，可得標題化合物（1.27g，產率59%)。泰 IR vmax (膜）3284 (br)，292 1，2852，1752，1720，1 649，1632 cm'1. 400 MHz lU NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (30H，bs), 1·5 卜 1.63 (4H，m)，2.07 (1H，bs，OH)，2.52-2.57 (2H，m)，3.20 (1H，d，J = 2.9 Hz)，3.45 (1H，s)，3.35-3.41 (2H，m)，3.5 8-3.68 (3 H，m)，3.80 (1H，m)，3.91 (1H，m)， 4.07 (1H，m), 4.31 (1 H , m)，4 · 4 6 (1 H，d, J = 8.1 Hz), 4.94 (1H, m), 5.16-5.28 (2H, m), 5.86 (1H, m). · FABMS (陽離子）m/z，5 8 3 [M-H] +，607 [M + Na] + · (3) (E) — 1 —丙嫌基3 — O —癸基—2 — O— (3—氧基十四烷醯基）一 β— D—吡喃葡糖苷（第A a6工程）將（2 )所得化合物（1 1 Omg )，依實施例1 ( 6 )之方法反應，可得標題化合物（ll〇mg，產率100%)。 IR vmax (膜）3500-3200，2922，2 8 5 3，1 745，1 720，1682 (w)， 1 648 (w), 1 630 (w) cm"1. -209 - 200413400 400 MHz lR NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 (30H, bs)，1.51-1.62 (7H，m,含 3H，d，J二5.9 Hz，at δ 1.54 ppm)，2.02 (1H, bs，OH)，2.52-2.58 (2H，m)，3·19 (1H，d， J=10.3 Hz)，3.3 6-3.48 (3 H，m，含 2H，s，at δ 1.45 ppm), 3.57_3·70 (3H，m)，3·81 (1H，m)，3.93 (1H，m)，4.62 (1H，d， J = 8.1 Hz)，4.99 (1H，m), 5.10 (1H，m)，6.16 (1H，dd，J=1.5, 12.5 Hz). FABMS (陽離子）m/z, 607 [M + Na] + . (4) (E) — 1 一丙烯基6— 0—(第三丁二甲矽烷基） —3— 〇 —癸基—2— 0— (3 —氧基十四烷醯基）—β— D — 毗喃葡糖苷（第A a 7工程）將（3 )所得化合物（1 1 7 m g，0 · 1 8 8 m m ο 1 )，依實施例1 (7 )之方法反應，可得標題化合物（1 15mg，產率87% ) 0 IR vmax (膜）3507 (br)，2927，2856，1754，1 682 (w)，1663 (w), 1621 (w), 1465 cm'1. 400 MHz lH NMR (CDC13) δ 0.08 (6H, s), 0.86-0.91 (15H, m，含 9 H，s , a t δ 0 · 9 0 p p m)，1 · 2 5 (3 0 H，b s), 1.5 0 -1.6 1 (5 H， m), 2.55-2.58 (2H, m), 3.12-3.20 (1H, m), 3.36-3.46 (3H, m), 3.54-3.73 (3H, m), 3.83-3.93 (2H, m), 4.57 (1H? d, J = 8.8 Hz), 4.98 (1H, m), 5.08 (1H, m), 6.14 (1H, d, J = 10.7 Hz). FABMS (陽離子）m/z，697 [M-H] +，721 [M + Na]+ (加入 Nal). -210 - 200413400 (5) (E) — 1 一丙燃基4一〇_嫌丙氧羯基一 6 — Ο—( 第三丁二甲矽烷基）一3—0—癸基一 2 — 〇—（3—氧基十四烷醯基）一 β - D—吡喃葡糖苷（第A a8工程）將（4 )所得化合物（950mg, 1.3 60mmol )，依實施例1 (8 )之方法反應，可得標題化合物（720mg，產率68% ) 之油狀物質。 IR Vmax (膜）2927，2856，1 75 8，1 682 (w)，1 664 (W)，1628 (w), 1464 cm'1 . 400 MHz ]H NMR (CDC13) δ 0.04 (6H, s), 0.86-0.90 (15H, m，含 9H，s，at δ 0·88 ppm)，1 · 2 6 (3 OH，b s )，1.42-1.60 (7H, m，含 3 H，d，J = 7 · 3 H z , a t δ 1.52 ppm), 2.54 (2H, t, J = 7.3 Hz), 3.19 (1H，d，J = 8.8 Hz), 3.43 (1H，s)，3.47-3.57 (4H， m), 3.72-3.73 (2H, m), 4.57 (1H, d, J = 8.1 Hz), 4.61-4.65 (2H，m)，4.78(lH，t，J = 9.5Hz)，4.97-5.14(2H，m)，5.27-5.39 (2H, m), 5.92 (1H, m), 6.16 (1H, dd, J=1.5, 12.5 Hz). FABMS (陽離子）m/z，805 [M + Na] + . (6) 4 —〇一烯丙氧羰基一 3—0 —癸基一2 — O— (3 — 氧基十四烷醯基）一 D-吡喃葡糖（第A a 10工程）將（5 )所得化合物（2.98g，3.95mmol )，依實施例10 (6 )之方法反應，可得標題化合物（2 · 1 6 g，產率5 8 % ) 〇 IR vmax (膜）2430 (br)，2925, 2855，1 7 54，1719，1 650 (w), 14 6 6 cm"1. 400 MHz !H NMR (CDC13) δ 0.88 (6H, t, J = 6.6 Hz), 1.26 -211 - 200413400 (30H, bs)，1.45- 1.70 (4H，m)，2.50-2.57 (2H, m)，3.47-3.80 (7H，m), 3.90 (1H，d，J = 9.5 Hz)，4.02 (1H，m)，4·66 (2H，d, J = 5.9 Hz), 4.76-4.8 8 ( 1.5H, m), 5.29-5.40 (2H, m), 5.49 (0.5H, bs), 5.93 (1H, m). FABMS (陽離子）m/z，3 69，611，651 [M + Na] + . HRFABMS C34H60O10Na 計算値：65 1.4085。實測値： 65 1 .4052. (7) 4 - O—燦丙氧鑛基一3 - O —癸基—6 - 〇— {2-去氧—4— 0 —二烯丙膦酸基一 3— 0—〔（R) — 3 —甲氧癸基〕一 6— 0—甲基一 2—〔（2，2，2—三氯乙氧羰基）胺基〕-β—D—吡喃葡糖基2—0- (3-氧基十四烷醯基）一 D-吡喃葡糖（第C Cl工程）將（6)所得化合物（64 1mg，1.0 19mmol)及實施例1 ( 10 )所用亞胺酸酯（877mg，1.04mmol )，依實施例1 ( 1〇 )之方法反應，可得標題化合物（1.30g，產率97%)。 IR vmax (膜）3500-3200，2927，2856，1 753，1737，1721 (肩） cm"1. 400 MHz lE NMR (CDC13) δ 0.88 (9H, t, J = 6.6 Hz), 1.26 (40H，bs)，1.40- 1.50 (4H，m)，1.57- 1.63 (2H，m)，1·70-1·78 (2H，m), 2.5 卜2·55 (2H，m)，3.35-3.8 8 (24H，m，含 2 個 3H， s, at δ 3.27 and 3.39 ppm), 4.18-4.30 (2H, m), 4.55 (0.5H, m), 5.25 -5.43 (6.5H, m), 5.89-5.99 (3H, m), 6.65 (1H, br). FABMS (陽離子）m/z，1 330 [M + Na，35C1] +，1 3 3 2. HRFABMS C61H 1 0 5 3 5 Cl3NO20PNa 計算値：1 3 30.593 1。實測 -212 - 200413400 値：1330.5928. (8) 4 - Ο —烯丙氧羰基一 3— Ο -癸基一 6 - 0 - {2 - 去氧一4一 Ο —二烯丙膦酸基一3 — 0—〔（R) — 3 —甲氧癸基〕一6— 0 —甲基—2—〔（Ζ) - 11一（十八碳烯醯基）胺基〕一 β— D—吡喃葡糖基}一2_0—（3 —氧基十四烷醯基）一 D—卩比喃匍糖（第C c2工程）將（7 )所得化合物（1.290g，〇.985mmol )，依實施例1 (1 1 )之方法反應，可得油狀標題化合物（75 6mg，產率 5 5%)。 φ IR vmax (膜）3305 (br)，2926，2856，1 755，1 652，1 543，1465 cm’1· 400 MHz lU NMR (CDC13) δ 0.88 (12H, m), 1.26 (60H, bs), 1.40-1.80 (10H, m), 2.01-2.02 (4H, m), 2.16-2.22 (2H, m), 2.52-2.59 (2H，m), 3.04-4.37 (25H，m，含 2 個 3H，s, at δ 3.27 and 3.39 ppm), 4.54-4.78 (7H, m), 5.00m (0.5 H, s), 5.23-5.52 (8.5H, m), 5.86-5.98 (3H, m), 6.09 (1H, d, J = 7.3 Hz, NH). 籲 FABMS (陽離子）m/z，1420 [M + Na] + . HRFABMS，C76H136N019PNa 計算値：1420.9342。實測値·· 1420.9347. (9) 二燦丙鱗酸基4一 Ο-燦丙氧鑛基—3— 0 —癸基一 6 —0— {2 —去氧一 4一 0 —二烯丙膦酸基一 3— Ο—〔（R)— 3—甲氧癸基〕一6— 0 —甲基一 2—〔（Ζ) — 11—(十八碳烯醯基）胺基〕一 β— D-吡喃葡糖基}一 2— 0 —（3-氧 -213 - 200413400 基十四烷醯基）一 α-D—吡喃葡糖苷（°^體）及二烯丙膦酸基 4— 0 —烯丙氧羰基一3 — 〇—癸基一 6— 0 — {2 —去氧一 4—0 —二烯丙膦酸基一 3—0—〔（R) — 3—甲氧癸基〕一 6— 〇 —甲基一 2 —〔（Z) — 11一（十八碳烯醯基）胺基〕一β— D—吡喃葡糖基}— 2— 0— (3—氧基十四烷醯基）一 β— D—吡喃葡糖苷（β體）（第Ca4工程）將（8 )所得化合物（743 mg，0.531 mmol )，依實施例1 (13 )之方法反應，可得標題化合物cx體（166mg，產率 20%)及β體（185mg,產率22%)油狀物。 α體·· IR vmax (膜）3306，3086 (w)，2926, 2856，1 759，1721，1 666, 1 548 cm-1. 400 MHz lH NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (60H, bs), 1.46- 1.73 ( 10H, m), 2.00-2.05 (4H, m), 2.21-2·24 (2H，m)，2·53 (2H，t，J = 7.7 Hz)，3.24-3.79 ( 1 9H，m，含 2 個 3H，s, at 3.28 and 3·38 ppm)，3·88-3·98 (2H, m)，4·08 (1H, m), 4.27 (1H, m), 4.54-4.65 ( 1 1H, m), 4.75-4.83 (2H, m), 5.24-5.42 ( 12H, m), 5.80 (1H, dd, J = 3.7, 6.6 Hz), 5.89-5.99 (5H, m), 6.54 (1H, d, J = 7.3 Hz, NH). FABMS (陽離子）m/z，1 558 [M + H] +，1 5 80 [M + Na] + . HRFABMS，C82H145N022P2Na 計算値：1 5 8 0 · 9 6 3 2。實測値 :1580.9617. β體： IR vmax (膜）3309，308 6 (w)，2926, 2856，1 759，1722，1 669, -214 - 200413400 1 550 cm'1. 400 MHz ]H NMR (CDC13) δ 0.88 (12H, t, J = 6.6 Hz), 1.26 (60H，bs)，1.38- 1.70 ( 1 0H,m)，2.00-2.04 (4H，m)，2.21-2·23 (2H，m), 2·53 (2H，t，J = 7.4 Hz)，3.2 卜 3·79 (21H，m,含 2 個 3H，s, at 3.27 and 3.38 ppm), 3.98 (1H, m), 4.27 (1H, m)，4.46-4.72 (12H，m), 5.00-5.09 (2H，m)，5.23-5.42 ( 1 2H， m), 5.85-5.98 (5H，m)，7·35 (1H，d，J = 9.5 Hz，NH). FABMS (陽離子）m/z，1 580 [M + Na]' HRFABMS，C82H145N022P2Na 計算値：1 580.9632。實測値：1580.9650. (10)鱗酸基3— O—癸基—6— O - {2 —去氧—3— Ο — 〔（R) — 3 —甲氧癸基〕一6— Ο—甲基一2—〔（Ζ)— 11—(十八碳烯醯基）胺基〕—4一 Ο —膦酸基一 β— D-吡喃葡糖基}— 2— Ο —（3-氧基十四烷醯基）一 a— D—吡喃葡糖苷（第C a5工程）將（9)所得化合物α體（178mg，0.114mmol)，依實施例1 ( 14)之方法反應，可得粉狀標題化合物（89mg,產率 5 9 % )。 IR vmax (KBr) 3286 (br)，2925，2854，1747，1717，1 630， 15 5 1，1466 cm"1. 400 MHz NMR (C D C13 - C D 3 〇 D , 5:1) δ 0.88 (12H, t, J = 6.6 Hz), 1.27 (60H, bs), 1.40-1.75 (10H, m), 2.00-2.04 (4H, m), 2.22-2.35 (2.5H, m), 2.58 (1.5H, t, J = 7.3 Hz), 3.24-4.10 (24H, m), 4.69 (1H, m), 4.76 (1H, d, J = 8.1 Hz), -215 - 200413400 5.3 3 -5.3 6 (2H, m), 5.67 (1H, m). FABMS (陰離子）m/z，1312 [M-H]·· C66H125N〇2〇P2 分析計算値：C, 60.30; H，9.58; N, 1.07; P， 4.7 1。實測値：C，5 9 · 8 7 ; Η，9 · 6 4 ; N，1 · 4 1 ; P , 4.6 5 · 〔實施例22〕鱗酸基3 — Ο —癸基一 6 — Ο — { 2 —去氧一3— 0—〔（R) —3 —甲氧癸基〕一6— 0 —甲基一 2—〔（Ζ) — 11—(十八碳烯醯基）胺基〕一 4 一 Ο -膦酸基一 β — D -吡喃葡糖基 }一2-0-（3-氧基十四烷醯基）一 β— D-吡喃葡糖苷（第C a 5工程）將實施例21 ( 9)所得化合物β體（160mg，0.103mmol) ，依實施例1 ( 1 4 )之方法反應，可得粉狀標題化合物（ 9 7 m g ,產率 7 2 % ) ° IR vmax (KBr) 3287 (br), 2925, 2854, 1 746，1717，1 629, 1554, 1466 cm"1. 400 MHz !H NMR (CDCI3-CD3OD, 5:1) δ 0.88 (12H, t, J = 6.6 Hz)，1.26 (60H, bs), 1.40-1.73 ( 10H, m), 2.01-2.02 (4H，m), 2.20-2.37 (2.5H，m)，2.58 (1.5H，t，J = 7.3 Hz)， 3.30-3.82 (2 1 H，m，含 2 個 3H，s at 3.30 and 3.41 ppm)， 4.01-4.05 (3H, m), 4.88-4.94 (2H, m), 5.05 (1H, m), 5.33-5.36 (2H, m). FABMS (陰離子）m/z，1312 [Μ-ΗΓ. C66H〗25N〇2()p2 分析計算値：C，60·30; H，9.58; N, 1.07; P， 4.7卜實測値：C, 59.93; H, 9.75; N, 1.29; P, 4.58. -216 - 200413400 〔試驗例1〕對人全血T N F α産生之抑制試驗（活體外）本試驗可依 H a r t m a η 之方法（D.A.Hartman，S.J.Ochalskiand R.P.Carlson; The effects of antiinflammatory and antiallergic drugs on cytokine release after stimulation of human whole blood by lipopolysaccharide and zymosan A: Inflamm. Res·，44, 269 (1995))來進行。從健康志願者有肝素存在下採末梢血。將全血3 60 mL注入預先添加被檢化合物之二甲亞礪溶液20jiL之96穴平板，次加刺激劑脂多糖（L P S )(源自大腸菌〇26 : B 6， Difco公司）（終濃度l〇ng/mL)20pL，充分混合，在37 °C及5% C〇2之條件下培養6小時。培養終了後，冷卻至4°C來中止反應，即以2000 r p m離心15分，將上清血漿分離回收。血漿中產生放出之TN Fa以酵素免疫測定（E L I S A )套組（B i 〇 s 〇 u r c e公司）測定。由被檢化合物之有或無存在下之細胞激動素產生量求得抑制率，基於這些平均抑制率，依最小自乘法求出I C 5q 値。結果示於如下。〔表1〕試驗化合物 I C 5G(nM) ^ 5 6 7-9 IX 2 3 4 5 6 V 8 IX 11 1- 1- 物物物物物物物物物物物物 -4ΛΪΛν-并\| ,Λ\— 戶〆 _ rflΛ\ - 4Λ 合合合合合合合合合合合合化化化化化化化化化化化化 0.16 0 • 3 1 0 • 3 7 0 • 019 0 • 20 1 2.2 0 • 63 3.2 0.6 -217 - 200413400 〔試驗例2〕對人全血T N F α産生之抑制試驗（活體外）依試驗例1之方法可求得試驗化合物之丨c 5()値。使用美國專利593 593 8號公報中記載之化合物爲比較化合物，與試驗化合物相同之方法求得丨c 5Q値。比較化合物之構造式如下：〇Me200413400 The residue was dissolved in diethyl ether (35 mL), and trimethylsilyldiazoline-a house-house solution (8. 23mL, 10% by weight, 4. 77 mm), and stirred for 45 minutes. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate, 10: 1) to obtain an oily compound. The obtained compound was dissolved in dry tetrahydrofuran (10 ni L), and a gasification cone (2 54 mg, 6. 6 9 m m ο 1), and after stirring for 1 hour under ice cooling, ethyl acetate was added. The obtained mixed solution was sequentially washed with a saturated ammonium chloride aqueous solution of water and saturated brine, dried over sodium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane: ethyl acetate, 4: 1) to obtain The title compound (533mg, 0. 934 mmol). ! H-NMR (400 MHz, CDC13) δ 0. 88 (3H, t, J = 6. 6 Hz), 1. 26- 1. 3 2 (3 6H, m), 1. 40 (3H, s), 1. 48 (3H5 s), 1. 53-1. 56 (4H, m), 2. 15 (1H, t, J = 5. 7 Hz, OH), 3. 40-3. 74 (9H, m), 3. 85-3. 89 (3H, m), 4. 10-4. 15 (1H, m). MS (FAB, positive) m / z, 59 3 (M + Na) +, 57 1 (M + H) +. HRMS (ESI, positive), calculated C34H66〇Na: 5 93. 4757; Found 値: 593. 4782. (3) (2,3-dioxoyl-12,4-6-isopropylidene-α-D-pyranosyl) diallyl mesophyl phosphate (Project F a4) (2) The obtained compound (5.33 mg, 〇. 9 3 4 mm ο 1) and reacted according to the method of Example 16 (4) to obtain the title compound (65 3 mg, yield 96%). 〇 1 Η-NMR (4 0 0 MHz, CDC 13) δ 0 . 88 (6 H, t, 1 = 6. 6 Hz), 1. 2 2-1. 2 6 (3 6 H, ni),]. 3 9 (3 H, s), 1. 4 7 (3 H, s), 1. 4 8-1. 5 8 200413400 (4H, m), 3. 2 9-3. 3 3 (1 H, m), 3. 42- 3. 72 (8H, m), 3. 84-3. 87 (1H, m), 4. 21-4. 28 (2H, m), 4. 3 5 -4. 40 (1 H, m) 5 4. 53-4. 58 (4H, m), 5. 25-5. 40 (4H, m), 5. 90-6. 00 (2H, m) · MS (FAB, positive) m / z, 7 5 3 (M + Na) +, 73 1 (M + H) +. (4) (2,3-dioxoyl-12a-a-D-glucopyranosyl) diallyl mesophyl phosphate (Fa 5th project) The compound obtained in (3) (6 1 7 mg , 0. 8 4 4 m m ο 1), reacted according to the method of Example 16 (5), to obtain the title compound (346 mg, yield 59%) 〇-NMR (500 MHz, CDC13) δ 0. 8 8 (3 Η, t, J = 6. 8 Η z), 1. 26- 1. 29 (3 6Η, m), 1. 53-1. 61 (6Η, m), 3. 02-3. 03 (1 Η, m), 3. 42-3. 70 (9H, m), 3. 91-3. 93 (2H, m), 4. 17 (1H, dt, J = ll. 7, 2. 9 Hz), 4. 29-4. 31 (1H, m), 4. 38-4. 44 (1 H, m), 4. 55-4. 60 (4H, m), 5. 25-5. 40 (4H, m), 5. 92-5. 98 (2H, m). MS (FAB, positive) m / z, 713 (M + Na) +, 691 (M + H) +. (5) (6--0- {2-deoxy-4 10-diallylphosphonic acid group 3-0-[(R) -3 3-methoxydecyl] -6-0-methyl-1 2 — [(2,2,2-Trichloroethoxycarbonyl) amino] -β-D-glucopyranosyl-2--2,2-dioxoyl-12-a-D-glucopyranose Base) Disyl propyl methophosphate (Fb 1 process) The compound obtained in (4) (2 80mg, 0. 405 mm), and reacted according to the method of Example 16 (6) to obtain the title compound (206 mg, yield 37%). 〇1R vma X (ΪΙ 旲 J 3 2 8 4, 3 0 8 4, 2 9 2 6, 2 8 5 6, 1 7 4 9, 1 6 5 0, 1 4 5 5 cm _ 1 200413400 iH-NMR (500 MHz, CDC13) δ 0. 88 (9H, t, J-6. 8 Hz), 1. 26-1. 30 (42H, m), 1. 40-1. 61 (9H, m), 1. 68-1. 76 (2H, no, 3. 09 (1 H, d, J = 6. 8 Hz), 3. 2 3-3. 2 8 (4 H, m, including 3 H, s, a t 3. 2 8 ppm), 3. 35-3. 66 (13H, m, including 3H, s, at 3. 39 ppm), 3. 73-3. 79 (4H, m), 3. 8 8-3. 9 8 (3 H, m), 4. 14-4. 21 (2H, m), 4. 27-4. 39 (2H, m), 4. 55-4. 59 (8H, m), 4. 70-4. 81 (3H, m), 5. 23-5. 28 (4H, m), 5. 35-5. 40 (4 H, m), 5. 90-5. 99 (4H, m), 6. 19 (1H, b r. s). MS (FAB, positive) m / z, 1 3 92 (M + Na) +. HRMS (ESI, positive), calculated 値 C64H116Cl3N019PNa: 1 3 92. 65 82; Found 値: 1 392. 6602. (6) (6--0- {2-deoxy-4 10-diallylphosphonic acid group 3- 10-[(R) -3-methoxydecyl] -6-〇-methyl-1 — [(Z) -11 octadecenylamino] -β-D-glucopyranosyl} — 2,3-dione◦ Dodecyl-α-D-glucopyranosyl) Diallyl methophosphate (Project Fb2) The compound obtained in (5) (1 1 1 mg, 0. 0 8 0 9 m m ο 1) ′ was reacted according to the method of Example 16 (7) to obtain the title compound (60. 3 mg, yield 51%; ° IR vmax (131) 3 3 07, 3 08 5, 2925, 2 85 5, 1 7 3 9, 1 65 8, 1 6 3 6, 1 5 4 8 cm-1 * 1 Η-NMR (500 MHz, CDC 13) δ 0. 88 (12H, t, 1 = 6. 6 Hz), 1. 2 8-1. 7 6 (8 1 H, m), 1 · 9 9-2. 0 1 (4 H, m), 2. 1 7-2. 2 4 (2 H, m), -189-200413400 3. 28-3. 96 (20H, m, including 3H, s, at 3. 28 ppm, 3H, s, at 3. 38 ppm), 4. 13-4. 39 (5H, m), 4. 56 (8H, m), 5. 03 (1H? D, J = 8. 2 Hz), 5. 23 -5. 39 (8H, m), 5. 90-5. 99 (4H, m), 6. 44 (1H, d, J = 7. 4 Hz). MS (FAB, positive) m / z, 1 482 (M + Na) +. HRMS (ESI, positive), calculated 値 C79H147N018P2Na: 1 482. 999 1 •, measured 値: 1 1 4 8 2 · 9 9 9 1. (7) (6-〇一 {2-—Deoxy-3—〇-[(R) —3-Methoxydecyl] -6-〇-methyl-1 — [(Z) — 11-octadecyl Suspicious amine group]-4-0 monophosphonic acid group-β-D-[1 glucopyranosyl}-2, 3-212-dodecyl-α-D-glucopyranosyl) hydrogen Methyl phosphate (Project Fb3) The compound obtained in (6) (60. 3mg, 0. 0413 mmol), and reacted according to the method of Example 16 (8) to obtain the title compound (39. 4mg, yield 73%) ° IR vmax (KBr) 2955, 2924, 2854, 2345, 1 654, 1631 cnT1 · 4-NMR (400 MHz, CD30D + CDC13) δ 0 · 9 0 (1 2 H, t, J = 6.2 Hz), 1. 1 5- 1. 76 (78H, m), 2. 01-2. 04 (4H, m)? 2. 23-2. 32 (2H, m), 3. 25-3. 42 (8H, m, including 3H, s, at 3. 29 ppm, 3H, s, at 3. 39 ppm), 3. 5 2-3. 84 (1 2H, m), 3.98 (1H, d, J = 10. 3 Hz), 4. 04-4. 31 (5H, m), 4. 62 (1H, d, J = 10. 3 Hz), 5. 3 3 -5. 3 5 (2H, m). MS (ESI, negative) m / z, 1 298 (M-H)-. HRMS (ESI, negative), calculated 値 C67H13〇N018P2: 1 298. 8754; Actual measurement: 1 298. 876 1. [Example 1 8] -190-200413400 3-phosphonooxypropyl 6-0-{2-deoxy-3-◦-[(R)-3-methoxydecyl]-6-0-methyl -2-[(Z) — 11 octadecylamino]-4-0-phosphonic acid group-β-D-glucopyranosyl group-2, 3-2,110-dodecyl group-α- D-glucopyranoside (1) 3-hydroxypropyl 2,3-dioxoyl-12,6-isopropylidene-α-D-glucopyranoside (No. G a 1 Engineering) The allyl 2,3-diazyl-dodecyl-4,6--0-isopropylidene-a-D-glucopyranoside obtained from Example 13 (2) (3. 30g, 5. 5 3 mmol) was dissolved in tetrahydrofuran (25 mL), and a 9-φborane bicyclo [3 · 3 · 1] nonane (9-ΒΒΒΝ) in 0.5mol / L tetrahydrofuran solution (28mL, 14) was added under ice-cooling. . 0 mmol) and stirred at room temperature for 18 hours. The reaction solution was cooled at 0 ° C, and a 3 mol / L sodium hydroxide aqueous solution (50 mL) and 30% hydrogen peroxide water (18 mL) were added, and the mixture was stirred at room temperature for 3 hours, and extracted with ethyl acetate 3 times. It was washed with a saturated aqueous ammonium chloride solution and a saturated saline solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate, 7: 3) to obtain the title compound (3. 03g, yield 89%). IR vmax (CHC13) 3 506, 2927, 2855 cm-1 · W-NMR (500 MHz, CDC13) δ 0. 88 (6H, t, J = 6. 8 Hz), 1. 25- 1. 94 (48H, m, including 3H, s, at 1. 4 8 ppm, 3 H, s, at 1. 40 ppm), 2. 88 (1H, t, J = 6. 8, 4. 9 Hz, OH), 3. 28 (1H, dd, J = 3. 9, 7. 8 Hz), 3. 49-3. 85 (1 2H, m), 3. 96 (1H, m)? 4. 87 (1H, d, J = 3. 9 Hz). MS (FAB, positive) m / z, 65 3 (M + K) '637 (M + Na) +, 615 -191-200413400 (M + H) +. HRMS (ESI, positive), calculated 値 C36H7〇07Na: 637. 50 1 1; Measured 値: 637. 5034. (2) 3- (diallylphosphonic acidoxy) propyl 2,3-dioxoyl-12-yl-D-glucopyranoside (Project G a2 and Project G a3) will (1 ) The obtained compound (9 8 1 mg, 1.5 9 mm ο 1), according to Example 16 (4) and (. 5). The title compound was obtained (828 mg, yield 71%). IR vmax (CHC13) 3 600, 3 393, 2927, 285 5 cnT1 · · iH-NMR (500 MHz, CDC13) δ 0. 8 8 (6 H, t, J = 6 · 8 Hz), 1. 25-1. 3 3 (3 6H, m), 1. 53- 1. 59 (4H, m), 1. 71 (1H, brs, OH), 1. 97-2. 09 (3H, m, containing OH), 3. 26 (1H, dd, J = 3. 9, 9. 8 Hz), 3. 43 (1H, t, J = 8. 8 Hz), 3. 51-3. 75 (7H, m), 3. 83-3. 91 (3H, m), 4. 13 (1H, m), 4. 27 (1H, m), 4. 53-4. 57 (4H, m), 4. 89 (1H, d, J = 3. 9 Hz), 5. 25-5. 39 (4H, m), 5. 90-5. 98 (2H, m). MS (FAB, positive) m / z, 773 (M + K) +, 757 (M + Na) +, 735 (M + H) +. Call HRMS (ESI, positive), calculate 値 C39H7601 () P: 735. 5 1 75; Found 値: 735. 5180. (3) 3- (diallylphosphonic acidoxy) propyl 6-0- {2-deoxy-4 10-diallylphosphonic acid group 3-0-[(R) — 3-methoxy Decyl] -6-〇-methyl-1 2- (2 '2' 2-dioxanthionyl) -β-D Glucosyl} -2,3-dione Diyl_α-D-glucopyranoside (Project G b 1) -192-200413400 The compound obtained using (2) (603mg, 0. 821 mmol) and reacted according to the method of Example 16 (6) to obtain the title compound (616 mg, yield 53%). IR vmax (CHC13) 3450, 3088, 2928, 2873, 2856, 1 737 cm-1 · iH- NMR (500 MHz, CDC13) δ 0 · 8 8 (9 H, t, J = 6 · 8 H z), 1. 25- 1. 79 (54H, m), 1. 95-2. 06 (2H, m), 2. 78 (1H, d, J = 2. 9 Hz, OH), 3.24 (1H, dd, J = 3. 9, 9 · 8 Hz), 3. 28 (3H, s), 3. 30 (1H, m), 3. 39 (3H, s), 3.41-43-86 (17H, m), 4. 08 (1H, d, J = 8. 8 Hz), 4. 12-4. 24 (2H, m), 4. 29 (1H, q, J = 8. 8, 9. 8 Hz), 4. 52-4. 60 (8H, m), 4. 72, 4.76 (2H, ABq, J = 11. 7 Hz), 4.84 (1H, d, J = 3. 9 Hz), 4.87 (1H, d, J = 7. 8 Hz), 5. 24-5. 39 (8H, m), 5. 90-5. 98 (4H, m), 6. 03 (1H, brs, NH). MS (FAB, positive) m / z, 1452 (M + K) +, 1436 (M + Na) +. HRMS (ESI, positive), calculated 値 C66H120Cl3N020P2Na ·· 1436. 6844; Found: 1436. 6847. (4) 3- (diallylphosphonic acidoxy) propyl 6-〇-1 {2-deoxy-4-0-diallylphosphonic acid group 3_〇-1 [(R) — 3-methoxy Decyl] —6—〇-methyl-2 — [(Z) — 11-octadecenylamino] —β—D—pyranoglucosyl} —2,3— __ • 一〇— Decayl-a-D-glucopyranoside (Project Gb 2) Using the compound obtained in (3) (3 80mg, 0. 269 mmol) and reacted according to the method of Example 16 (7) to obtain the title compound (217 mg, yield 54%) ° IR vmax (CHC13) 3454, 33 19, 3089, 2928, 2856, 1 665 cm · 1 ·- 193-200413400 ^ -NMR (500 MHz, CDC13) δ 0 · 8 8 (1 2 H, t, J = 6 · 8 H z), 1. 25- 1. 80 (76H, m), 1. 95-2. 05 (6H, m), 2. 14-2. 27 (2H, m), 3. 17 (1H, d, J = 3. 9 Hz, 0H), 3. 21-3. 24 (2H, m), 3.28 (3H, s), 3. 30 (1H, m), 3. 38 (3H, s), 3. 41-3. 82 (15H, m), 3. 94 (1H, t, J = 9. 8, 8. 8 Hz), 4. 07 (1H, d, J = 8. 8 Hz), 4. 1 1-4. 20 (2H, m), 4. 25 (1H, q, J = 8. 8, 9. 8 Hz), 4. 52-4. 58 (8H, m), 4. 84 (1H, d, J = 3. 9 Hz), 5. 16 (1H, d, J = 7. 8 Hz), 5. 23-5. 39 (10H, m), 5. 90-5. 98 (4H, m)? 6. 36 (1H, d, J = 6. 8 Hz, NH). MS (FAB, positive) m / z, 1 542 (M + K) +, 1 526 (M + Na) + · HRMS (ESI, positive), calculated 値 C81H15iN019P2Na: 1 527. 026 1; Measured 値: 1 5 2 7. 0 2 7 7. (5) 3-Phosphonic acid oxypropyl 6 —〇一丨 2 —deoxy-3—〇 — [(R) —3 —methoxydecyl] 6 —〇-methyl-2 — [(Z) — 11-octadecylamino] -4-10 phosphono-β-D-glucopyranosyl-1,2,3-di-12-dodecyl_a_D-glucopyranoside (No. Gb3 Engineering) Using the compound obtained in (4) (200 mg, 0.13 mm), the reaction was carried out according to the method of Example 16 (8) to obtain the title compound (150 mg, yield 84%) ° IR vmax (KBr) 3285, 3228, 3069, 3004, 2955, 2924, 285 3, 2 3 18cm · 1 · ^ -NMR (500 MHz, CD3OD + CDCI3) δ 0 · 8 9 (1 2 H, t, J = 6 8 Hz), 1. 30- 1. 67 (74H, m), 1. 72- 1. 75 (2H, m), 1. 93-1. 99 (2H, m), 2. 01-2. 04 (4H, m), 2. 20-2. 30 (2H, m), 3. 17 (1H, dd, J = 3. 9, 9. 8 Hz), 3. 29 (3H, s), 3. 33 (1 H, m), 3.39 (3 H, s), -194-200413400 3. 44 (1H, t, J = 9. 8, 8. 8 Hz), 3. 48-3. 67 (10H, m)? 3. 73-3. 85 (6H, m), 4. 04-4. 12 (4H, m), 4. 48 (1H, d, J = 8. 8 Hz), 4. 85 (1H, d, J = 2. 9 Hz), 5. 31-5. 38 (2H, m). MS (ESI, negative) m / z, 1342 (M-H) ·. HRMS (ESI, negative), calculated 値 C69H134N019P2: 1342. 903 1; Measured 値 * 1342. 9047. [Example 1 9] 2-phosphonoethyl 6-0- {2-deoxy-3-0-[(R) -3-3-methoxydecyl] -6-0-methyl-1 2-[( Z) — 11 —octadecylamino] — 4 —0-phosphonic acid group — β — D —glucopyranosyl — 2, 3 — 0 — 1212yl — β — D-glucopyranosyl Glycoside (1) Allyl 4,6--0-isopropylidene-β-D-glucopyranoside (Project A c 3) Using allyl 2,3,4,6--0-tetraacetamidine Β-D-glucopyranoside (Carbohydr. Res. , 203, 34 1-342 (1 99 1), known compounds) (8. 00g, 20. 6mm〇l), according to the method of Example 16 (1), the title compound (4. 52 g, yield 84%). IR vmax (KBr) 3493, 3285, 3082, 2993, 292 1, 2882 cm'1 · ^ -NMR (500 MHz, CDC13) δ 1 · 44 (3 H, s), 1 · 5 1 (3 H, s ), 2. 82 (1H, d, J = 2. 9 Hz, OH), 2. 94 (1H, d, J = 2. 0 Hz, OH), 3. 27 (1H, td, J = 5. 9, 9. 8 Hz), 3.48 (1H, m), 3.59 (1H, t, J = 8. 8, 9. 8 Hz), 3. 65 (1H, m), 3. 80 (1H, t, J = 9. 8, 10. 7 Hz), 3. 93 (1H, dd, J = 5. 9, 10. 7 Hz), 4. 13 (1H, dd, J = 5. 9, 12. 7 Hz), 4. 36 (1H, dd, J = 5. 9, 12. 7 Hz), 4. 40 (1H? D, J = 7. 8 Hz), -195-200413400 5. 22-5. 34 (2H, m), 5. 93 (1H, m). MS (FAB, positive) m / z, 299 (M + K) +, 28 3 (M + Na) +, 261 (M + H) +. HRMS (ESI, positive), calculated 値 C12H2G06Na: 283. 1 169; Measured 値: 2 8 3 · 1 1 5 3. (2) Allyl 2,3-dioxoyl-12,6-isopropylidene-β-D-glucopyranoside (Project A C2) Use the compound obtained in (1) ( 4. 25g, 16. 3mm〇l), according to the method of Example 16 (2), the title compound (5. 33g, yield 55%) ° 11 ^^ ((: 11 (: 13) 2927, 2855 please -1-^ -NMR (500 MHz, CDC13) δ 0 · 8 8 (6 Η, t, J = 6 · 9 Η z), 1. 26- 1. 3 3 (3 6Η, m), 1. 40 (3H, s), 1. 47 (3H, s), 1. 52-1. 59 (4H, m), 3. 12 (1H, t, J = 7. 8, 8. 0 Hz), 3. 16 (1H, td, J = 4. 9, 9. 8 Hz), 3. 62-3. 68 (2H, m), 3. 71-3. 82 (3H, m), 3. 90 (1H, dd, J = 4. 9, 10. 7 Hz), 4. 11 (1H, dd, J = 5. 9, 12. 7 Hz), 4. 34 (1H, dd, J = 5. 9, 12. 7 Hz), 4. 37 (1H, d, J = 7. 8 Hz), 5. 18-5. 34 (2H, m), 5. 90 (1H, m). MS (FAB, positive) m / z, 635 (M + K) +, 619 (M + Na) +, 595 (Μη) 'HRMS (ESI, positive), calculated 値 C36H6806Na: 619. 4911; Measured 値: 619. 4919. (3) 2-Hydroxyethyl 2,3-dioxoyl-12,6-6- ◦ isopropylidene-β-D-glucopyranoside (Abl Project) -196-200413400 Use ( 2) The obtained compound (3. 8 1g, 6. 38 mmol) and reacted according to the method of Example 16 (3) to obtain the title compound (3.25 g, yield 85%). 0 IR vmax (KBr) 3484, 2996, 2919, 285 1 cm · 1 · J-NMR (500 MHz, CDC13) δ 0 · 8 8 (6 H, t, J = 6 · 8 H z), 1. 26- 1. 3 3 (3 6H, m), 1. 40 (3H, s), 1. 48 (3H, s), 1. 52-1. 60 (4H, m), 2. 72 (1H, t, J = 5. 9-6. 8 Hz, OH), 3. 14 (1H, t, J = 7. 8, 8. 8 Hz), 3. 20 (1H, td, J = 9. 8, 4. 9 Hz), 3. 29 (1H, t, J = 8. 8, 9. 8 Hz), 3. 55 (1H, t, J = 9. 8 Hz), 3. 62 (1H, m), 3. 71-3. 78 (6H, m), 3. 80-3. 92 (3H, m), 4. 40 (1H, d, J = 7. 8 Hz). MS (FAB, positive) m / z, 639 (M + K) +, 623 (M + Na) '601 (M + H) +. HRMS (ESI, positive), calculated 値 C35H6807Na: 623. 4859; Measured 値: 623. 4869. (4) 2-Bromoethyl 2,3-dioxalyl-12,6-isopropylidene-β-D-glucopyranoside (Project D a 1) will be (3) The resulting compound (1. 95 g, 3. 25 mmol) was dissolved in dichloromethane (15mL), and carbon tetrabromide (1. 40g, 4. 22mm〇l) and triphenylphosphine (1. 29g, 4. 92 mmol), and stirred at room temperature for 1 hour. The reaction solution was diluted with dichloromethane, washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane · ethyl acetate, 9: 1) to obtain the title compound (2. 01 g, yield 93%). IR vmax (CHC13) 2927, 2855 cm'1 · 4-NMR (500 MHz, CDC13) δ 0 · 8 8 (6Η, t, J = 6 · 8 Ηz), -197-200413400 1. 26- 1. 34 (36H, m), 1. 40 (3H, s), 1. 47 (3H, s), 1. 52-1. 59 (4H, m), 3. 10 (1H, t, J = 7. 8, 8. 8 Hz), 3. 17 (1H, td, J = 4. 9, 9. 8 Hz), 3. 26 (1H, t, J = 8. 8 Hz), 3. 48 (2H, t, J = 6. 8 Hz), 3. 54 (1H, t, J = 8. 8, 9. 8 Hz), 3. 61-3. 66 (2H, m), 3. 71-3. 76 (2H, m), 3. 81-3. 90 (3H, m), 4. 13 (1H? M), 4. 37 (1H, d, J = 6. 8 Hz). MS (FAB, positive) m / z, 685 (M + Na) +, 66 1 (M-H) +. HRMS (ESI, positive), calculated 値 C35H67Br06Na: 685. 4030; Actual measurement: 685. 3994 · (5) 2- (diallylphosphono) ethyl 2,3-dioxalyl-12-D-glucopyranoside (Project D a2 and Project D a3) will ( 4) The obtained compound (1. 78g, 2. 68mm〇l) was added triallyl phosphite (10mL), heated and stirred under nitrogen and 180 ° C for 2 hours, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane: ethyl acetate, 2: 3) Get the mixture (2. 28g). The mixture was dissolved in an 80% acetic acid aqueous solution (15 mL), stirred at 60 ° C for 2 hours, concentrated under reduced pressure, and diluted with ethyl acetate. It was washed with water, saturated aqueous sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (ethyl acetate: ethanol, 20: 1) to obtain the title compound (834 mg, yield 44%). IR vmax (film) 33 94, 3085, 2925, 2855 cnT1 ·] H-NMR (500 MHz, CDC13) δ 〇 · 8 8 (6 Η, t, J = 6 · 9 Η z), 1. 26- 1. 3 1 (36Η, m), 1. 51-1. 61 (4H, m), 1. 71 (1H, brs, OH), 2. 21 (2H, dt, J = 7. 8, 19. 5 Hz), 2. 57 (1H, brs, OH), 3. 06 (1H, t, J = 7. 8, 8. 8 Hz), 3. 19 (1H, t, J = 8. 8, 9. 8 Hz), 3. 45 -198-200413400 (1H, m), 3. 55 (1H, m), 3. 63 (1H, m), 3. 71-3. 91 (5H, m), 4. 10 (1H? M), 4. 3 3 (1H, d, J = 6. 8 Hz), 4 · 5 2-4. 5 6 (4H, m), 5. 24-5. 3 8 (4H, m), 5. 91-5. 97 (2H, m). MS (FAB, positive) m / z, 743 (M + K) +, 727 (M + Na) +. HRMS (ESI, positive), calculated 値 C38H73 09PNa: 727. 4 8 80; Found 値: 727. 4916. (6) 2- (diallylphosphonic acid) ethyl 6-0- {2-deoxy-4-10-diallylphosphonic acid 3-3-00-[(R) — 3-methoxydecane Group] -6-0-methyl-2 2-[(2,2,2-trichloroethoxycarbonyl) amino] -β-D-glucopyranosyl} -2,3-dione Diyl-β-D-glucopyranoside (Project D b 1) Using the compound obtained in (5) (390 mg, O. 541 mmol), and reacted according to the method of Example 16 (6) to obtain the title compound (486 mg, yield 64%) ° IR vmax (CHC13) 3257,308 8,2928,287 3,2856,1740 cm-1 · W-NMR (500 MHz, CDC13) δ 0 · 8 8 (9 H, t, J = 6 · 8 H z), 1. 26- 1. 78 (54H, m), 2. 16-2 · 27 (2H, m), 2.48 (1H, s, OH), 3. 01 (1H, t5 J = 7. 8, 8. 8 Hz), 3. 12 J = 8. 8 Hz), 3. 23- 3.29 (5H, m, including 3H, s, at 3. 27 ppm), 3. 36-3. 41 (4H, m, including 3H, s, at 3. 40 ppm), 3. 45 -3. 56 (3 H, m), 3. 60-3. 70 (3H, m), 3. 74-3. 91 (7H, m), 4. 14-4. 16 (2H, m), 4. 23 (1H, d, J = 6. 8 Hz), 4. 28 (1H, q, J = 9. 8 Hz), 4. 51-4. 60 (8H, m), 4. 63 (1H, ABq, J = 11. 7 Hz), 4. 74 (1H, d, J = 7. 8 Hz), 4. 86 (1H? ABq, J = 1 1. 7 Hz), 5. 24-5. 3 9 (8H, m), 5. 89-5. 98 (4H, m), 7. 00 -199-200413400 (1 H, brs, NH). MS (FAB, positive) m / z, 1 422 (M + K) +, 1 406 (M + Na) +, 1384 (M + H) +. HRMS (ESI, positive), calculated: C65H118Cl3N019P2Na: 1406. 6747; Found 値: 1406. 6772. (7) 2- (diallylphosphonic acid) ethyl 6-0- {2-deoxy-4-0-diallylphosphonic acid 3-0-[(R) — 3-methoxydecane [] [6-Z-methyl-2] [(Z) — 11 Octadecenylamino] -β-D-glucopyranosyl} -2,3-dioxoyl One β-D-glucopyranoside (Project D b 2) Using the compound obtained in (6) (429 mg, 0.1 309 mmol), and reacted according to the method of Example 16 (7) to obtain the title compound (203 mg, yield 45%) ° IR vmax (CHC13) 3452, 3302, 3088, 2928, 2856, 1 664 cm'1 · ^ -NMR (500 MHz, CDC13) δ 0. 88 (12H, t, J = 6. 8 Hz), 1. 25-1. 78 (76H, m), 1. 99-2. 01 (4H, m), 2. 14-2. 32 (4H, m), 3. 02 (1H, t, J = 7. 8, 8. 8 Hz), 3. 08 (1H? D, J = 3. 9 Hz, OH), 3.14 (1H, t, J = 7. 8, 8 · 8 Hz), 3 · 22-3. 33 (5H, m, including 3H, s, at 3. 28 ppm), 3. 36 (1H, m), 3. 38 (3H, s), 3. 52-3. 5 8 (2H, m), 3. 60-3. 86 (1 0H, m), 3. 93 (1H, t, J = 8. 8, 9. 8 Hz), 4. 03 (1H, m), 4. 10 (1H, d, J = 9. 8 Hz), 4. 23 (1 H, d, J = 7 · 8 H z), 4 · 2 6 (1H, q, J = 9. 8 Hz), 4. 51-4. 61 (8H, m), 5. 13 (1H, d, J = 8. 8 Hz), 5. 23-5. 3 8 (1 0H, m), 5. 90-5. 97 (4H, m), 6.65 (1H, m, NH). -200-200413400 MS (FAB, positive) m / z, 1512 (M + K) +, 1 496 (M + Na) + · HRMS (ESI, positive), calculated 値 C8〇H149N018P2Na: 1497. 01 27; Actual measurement: 1497. 0092. (8) 2-Phosphonic acid ethyl 6-0- {2-deoxy-3-0-[(R) -3-methoxydecyl] -6-6-methyl-1 2-[(Z) — 11-octadecylamino] -4 10-phosphono-β-D-glucopyranosyl} -2,3-di-12-dodecyl-β-D-pyranoglucoside (No. Db3 project) Using the compound obtained in (7) (1.88 mg, 0.18 mm), the reaction was carried out according to the method of Example 16 (8) to obtain the title compound (14 lmg, yield 84%). IR vmax (KBr) 3413, 3287, 307 1, 3005, 2955, 2924, 2853, 2345, 1630 CDT1 ·] H-NMR (500 MHz, CD3OD + CDCI3) δ 0 · 9 0 (1 2H, t, J 2 6 . 8 Hz), 1. 29-1. 65 (74H, m), 1. 73- 1. 77 (2H, m), 2. 01-2. 03 (4H, m), 2. 12-2. 18 (2H, m), 2. 25 (2H, t, J = 7. 8 Hz), 2. 99 (1H, t, J = 7. 8, 8. 8 Hz), 3. 15 (1 H, t, J 2 8 · 8 H z), 3 · 2 9-3 · 3 7 (4 H, m, including 3H, s, at 3. 31 ppm), 3. 41 (3H, s), 3 · 5 7-3. 8 7 (1 5 H, m), 4. 03-4. 12 (3H, m), 4. 28 (1H, d, J = 6. 8 Hz), 4. 62 (1H, d, J = 7. 8 Hz), 5. 3 1-5. 37 (2H, m). MS (ESI, negative) m / z, 1312 (M-H) ·. HRMS (ESI, negative), calculated 値 C68H132N018P2: 1 3 1 2. 8923; Measured radon: 1 3 1 2. 8 9 3 1. [Example 20] 2- (phosphonooxy) ethyl 3- 0_decyl-6-0 — {2 —deoxy-3 -201-200413400 —O— [(R) — 3 —methoxydecane Group]-6-0-methyl-1 2-[(Z) -1 1 1 (octadecyl group) amine group]-4-0-Linosyl-β-D-Gluranosyl} — 2-0- (3-oxytetradecylamino) -a-D-glucopyranoside (1) 2-hydroxyethyl 3-0-decyl-4,6--0-isopropylidene- α-D-glucopyranoside (Project H a 1) The allyl 3-0-decyl-4,6--0-isopropylidene-a-D-pyran obtained in Example 1 (3) Glucoside (2. 20g, 5. 491 mmol) was dissolved in acetonitrile-carbon tetrachloride-water (2: 2: 3, 280mL), and sodium periodate (30g, 0. 140 mol) and catalytic amount of ruthenium oxide (lOOmg, 0. 751 mmol), stirred vigorously 1. 5 hours. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate, and concentrated by filtration. Dissolved in DMF (5 OmL), forcefully insert triethylamine (2. 00g, 19. 762mmol) and brominated allyl (2. 45g, 20. 25 1 mm〇l), and stirred at 50 ° C for 1.5 hours. The reaction was diluted with ethyl acetate, washed with dilute hydrochloric acid, water and sodium bicarbonate solution, and dried over magnesium sulfate. It was concentrated by filtration and purified by silica gel column chromatography. Dissolve cyclohexane-ethyl acetate (3: 1, then 1: 1) to obtain the allyl ester, ketone and aldehyde mixture 1. 734g. The mixture was dissolved in ethanol (25 mL), and sodium borohydride (300 mg, 7. 9 3 m m ο 1), and stirred at room temperature for 3 hours. The residual sodium borohydride was decomposed with acetic acid and diluted with ethyl acetate. Wash with dilute hydrochloric acid, water and sodium bicarbonate solution, and dry under magnesium sulfate. It was concentrated by filtration and purified by silica gel column chromatography. Dissolve cyclohexane-ethyl acetate (3: 1) to obtain the title compound (1. 197 g, 54% yield). IR vmax (II) 3 396 (br), 2994, 2926, 2856 cm * 1. -202-200413400 400 MHz lH NMR (CDC13) δ 0. 88 (3H, t, J = 6. 8 Hz), 1. 26 (14H, bs), 1.41 (3H, s), 1. 49 (3H, s), 1. 54- 1. 59 (2H, m), 2. 75 (1H, d, J = 5. 9 Hz, OH), 2. 90 (1H, bs, OH), 3. 50-3. 86 (12H, m), 4. 93 (1 H, d, J = 3 · 7 Hz). FABMS (cation) m / z, 405 [M + H] +, 427 [M + Na] +. (2) 2- (Diallylphosphonic acidoxy) ethyl 3-O-decyl-4,6-O-isopropylidene-α-D-glucopyranoside (Project H a 2) (1) The obtained compound (393 mg, 0.1 972mmol) was dissolved in dichloromethane (10mL), and 1H-tetrawa (102mg, 1. 457mmol, 1. 5 equivalents) and diallyl diisopropylamino phosphate (262 mg, 1. 069 mmol, 1.1 equivalents), and stirred at room temperature for 20 minutes. Tetrahydrofuran (10 mL) was added, and 30% hydrogen peroxide water (2010 ^) was added, followed by stirring at room temperature for 15 minutes. The reaction solution was diluted with ethyl acetate, washed with 10% sodium thiosulfate water, sodium bicarbonate solution and brine, and dried over magnesium sulfate. It was concentrated by filtration and purified by silica gel column chromatography. The title compound was obtained by dissolving cyclohexane-ethyl acetate (3: 1) (440 mg, yield 80%). IR vmax (film) 3409 (br), 2994, 2926, 2857 cnT1 · 400 MHz lU NMR (CDC13) δ 0. 88 (3H, t, J = 6. 6 Hz), 1. 26 (14H, bs), 1. 40 (3H, s), 1. 49 (3H, s), 1. 55- 1. 59 (2H, m), 3. 09 (1H, d, J = 8. 1 Hz, OH), 3. 44-3. 94 (1 0H, m), 4. 23-4. 28 (2H, m), 4. 55-4. 60 (4H, m), 4. 88 (1H, d, J = 3. 7 Hz), 5. 25-5. 30 (2H, m), 5. 36-5. 43 (2H, m), 5. 91-6. 02 (2H, m). (3) 2- (diallylphosphonic acidoxy) ethyl 3-O-decyl-4,6-O-isopropylidene-2-0- (3-oxytetradecanyl)- cx — D-pyridine-203-200413400 glucoside (Project H a3) The compound (2) obtained in (2) (440mg, 0. 779mmol) was dissolved in dichloromethane (3 OmL), and 3-oxytetradecanoic acid (280 mg, 0. 858 mmol) and 1-ethyl-3- (3-dimethylaminepropyl) -carbodiimide hydrochloride (179mg, 0. 935 mmol), stirred at room temperature for 40 minutes, concentrated, and diluted with ethyl acetate. Wash with sodium bicarbonate solution and brine, and dry under magnesium sulfate. It was concentrated by filtration and purified by silica gel column chromatography. Dissolve cyclohexane-ethyl acetate (1: 1) to obtain the title compound (464 mg, yield 75%). IR vmax (film) 2926, 2856, 1 750, 1719, 1 650 (w), 1 627 (w) · cm'1. 400 MHz lU NMR (CDC13) δ 0. 88 (3H, t? J = 6. 8 Hz), 1. 26 (22H, bs), 1. 39 (3H, s), 1. 40- 1. 63 (9H, m, including 3H, s, at δ 1. 49 ppm), 2. 53 (2H, t, J = 7. 3 Hz), 3. 40-3. 54 (3H, m), 3. 61-3. 75 (6H, m), 3. 82-3. 88 (2H, m), 4. 19-4. 23 (2H, m), 4. 56-4. 59 (4H, m), 4. 77 (1H, dd, J = 3. 7, 9. 5 Hz), 5. 03 (1H, d, J = 4. 4 Hz), 5. 26-5. 41 (4H, m), 5. 93-6. 00 (2H, m). FABMS (cation) m / z, 789 [M + H] +, 81 1 [M + Na] +. # HRFABMS, C41H73012PNa Calculation: 811. 4737. Measured 値: 8 1 1. 4724. (4) 2- (diallylphosphonooxy) ethyl 3-O-decyl-2-0- (3-oxytetradecanyl) -α-D-glucopyranoside (Part A Project b3) The compound obtained in (3) (460 mg, O. 5 8 3 mmol) was dissolved in 80% acetic acid water (46mL), and stirred at 85 ° C for 1. 5 hours. After the reaction was completed, the reaction -204-200413400 solution was concentrated and purified by silica gel column chromatography. Dissolve in methanol-ethyl acetate (1:19) to obtain the title compound (374 mg, yield 86%), oily compound 〇IR vmax (membrane) 3407 (br), 2925, 2855, 1 747 , 1718, 1 650 (w), 14 6 5 cm'1. 400 MHz! H NMR (CDC13) δ 0. 88 (3H, t, J = 6. 6 Hz), 1. 26 (30H, bs), 1.531.1. 60 (4H, m), 2. 51 -2.55 (3H, m, containing OH), 2.66 (1H, d, J = 2. 9 Hz, OH), 3. 46-3. 90 (1 1H, m, including 2H, s, at δ 3. 50 ppm), 4. 20-4. 25 (2H, m), 4. 55-4. 59 (4H, m), 4. 72 (1H, dd, J = 3. 7, 9. 5 Hz), 5. 08 (1H, d, J = 3. 7 Hz), 5. 26-5. 41 (4H? M), 5. 91-5. 99 (2H, m). FABMS (cation) m / z, 749 [M + H] +, 771 [M + Na] + · HRFABMS, C38H69012PNa Calculated 値: 77 1. 4425. Found 値: 77 1. 44 1 8. (5) 2 — (monopropionateoxy) ethyl 3 — 0 —decyl-6 — 0 — {2 deoxy- 4-0 —diallylphosphonic acid group 3 — 0 — [( R) — 3 —methoxydecyl] -6—0—methyl-1 2-[(2,2,2-trichloroethoxy) amino]] β-D_ [I than glucosyl} — 2-0— (3-oxytetradecylamino)-(X-D-glucopyranoside (Cbl Project)) The compound obtained in (4) (374mg, 0.1 49 9mmol) and the same imidate used in Example 1 (10) (422mg, 0. 4 99 mmol) and reacted according to the method of Example 1 (10) to obtain the title compound (486 mg, yield 68%). IR vmax (film) 3292 (br), 308 5 (w), 2927, 2856, 1 748, 1721, -205-200413400 1 650 (w), 1 545, 1460 cm " J. 400 MHz] H NMR (CDC13) δ 0. 88 (9H, t, J = 6. 6 Hz), 1. 26 (42H, bs), 1. 40- 1. 80 (8H, m), 2. 52 (2H, t, J = 7. 7 Hz), 2. 80 (1H, bs, OH), 3. 24-3. 84 (24H, m, including 2 3H, s, at δ 3. 29 and 3. 39 p p m), 4 · 0 9-4. 3 2 (4 H, m), 4 · 5 3-4 · 5 9 (8 H, m), 4 · 6 9-4. 7 1 (3H, m), 4. 87 (1H, m), 5. 03 (1H, d, J = 3. 7 Hz), 5. 24-5. 41 (8H, m), 5. 90-5. 99 (4H, m), 6.62 (4H, m), 6.36 (1H, bs, NH), FABMS (cation) m / z, 1450 [M + Na, 35C1] +, 1 45 2. HRFABMS C65H114Cl3N022P2Na Calculation 値: 1450. 6298. Found 値: 1450. 6301. (6) 2- (diallylphosphonic acidoxy) ethyl 3-O-decyl-6-O— {2 deoxy-4—0—one dipropionate—3—0— [( R) — 3-methoxydecyl] — 6 — 0 —methyl — [(Z) — 11- (octadecylphosphino) amino] — β — D —glucopyranosyl] — 2-0-(3-oxytetradecanyl) -α-D-glucopyranoside (Cb2 project) Use the compound obtained in (5) (477mg, 0. 334 mmol) and reacted according to the method of Example 1 (11) to obtain the title compound (412 mg, yield 81%) as an oil. IR vmax (film) 3302, 3086 (w), 2926, 2855, 1746, 1719, 1 654, 1 55 3, 1 465 cm · 1 · 400 MHz! H NMR (CDC13) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 26 (60H, bs), 1. 40- 1. 80 (10H, m), 1. 99-2. 02 (4H, m), 2. 17-2 · 27 (2H, m), 2. 52 (2H, m), 3. 20-3. 9 1 (26H, m, including 2 3H, 200413400 s, at δ 3. 29 and 3. 38 ppm), 4. 07-4. 27 (6H? M), 4. 54-4. 57 (8H, m), 4. 70 (1H, dd, J = 3. 7, 9. 5 Hz), 5. 02 (1H, d, J = 3. 7 Hz), 5. 19 (1H, d, J = 8. 1 Hz), 5. 23-5. 40 (1 0H, m)? 5. 88-5. 99 (4H, m), 6. 51 (1H, d, J = 6. 6 Hz, NH). FABMS (cation) m / z, 1518 [M + H] +, 1 540 [M + Na] + · HRFABMSC8〇HM5N〇2iP2Na Calculated 値: 1540. 9682. Found 値: 1540. 9653. (7) 2- (phosphonooxy) ethyl 3 — O —decyl-6 — 0 — {2 —deoxy-3 — 0 — [(R) — 3 —methoxydecyl] — 6 — 0 -Methyl- 2-· [(Z) — 11-(octadecylpyridinyl) amino]-4-0-glutamic acid-β-D-glucopyranosyl}-2-0- (3-oxytetradecylpyridyl) — α-D-glucopyranoside (Cb3 project) Use the compound obtained in (6) (200mg, 0. 132 mmol), and reacted according to the method of Example 1 (14) to obtain the title compound (150 mg, yield 84%). IR vmax (KBr) 3286 (br), 2925, 2854, 1742, 1716, 1 629 , 1 552, 1 466 cm'1. 400 MHz lH NMR (CDCI3-CD3OD, 5: 1) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 26 (60H, bs), 1. 40- 1. 63 (8H, m), 1. 72-1. 77 (2H, m), 1. 99-2. 04 (4H, m), 2. 18-2. 22 (2H, m), 2. 53-2. 57 (2H, m), 3. 30-3. 83 (24H, m, including 2 3 Η, s, at δ 3 · 3 0 an d 3. 41 ppm), 4. 01-4. 14 (4H, m), 4. 65-4. 72 (2H, m), 4. 98 (1H? D, J = 3. 7 Hz), 5. 30-5. 36 (2H? M). FABMS (anion) m / z, 1 3 56 [M-H] ·. -207-200413400 HRFABMS C80H145NO21P2Na Calculated 値: 1 540. 9682. Found 値: 1540. 9653. C68H129N021P2 Analysis and calculation: C, 60. 11; H, 9. 57; Ν, 1.03; P, 4. 56. Found 値: C, 59. 83; Η, 9. 75; N, 1. 21; P, 4. 38. [Example 2 1] Phosphonic acid group 3-O-decyl-6-O- {2-deoxy-3-O-[-((R) -3-methoxydecyl]]-6-O-methyl- 2-[(Z) — 11- (octadecenyl) amino] -4—0-phosphonic acid-β-D-glucopyranosyl} —2—0— (3-oxydeca Four-membered fluorenyl) -α-D-glucopyranose (1) allyl 3-0-decyl-4,6-0-isopropylidene-2-0 0 (3-oxytetradecane Alkyl) -β-D-glucopyranoside (Project A a4) The allyl 3-0-decyl-4,6-0-isopropylidene-β- obtained from Example 1 (3) D-glucopyranoside (401mg, l. OOmmol) was dissolved in methylene chloride (4mL), and triethylamine (150mg, 1. 48 mmol) and 3-oxo tetrafluoromethane (313 mg, 1. 20 mmol) of dichloromethane (2 mL) solution was reacted at room temperature for 2 hours and then diluted with dichloromethane. The dichloromethane solution was washed with a sodium bicarbonate solution and a saturated saline solution, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography. Dissolve cyclohexane-ethyl acetate (6: 1) to obtain the title compound (400 mg, yield 64%). IR vmax (film) 2923, 285 3, 1 752, 1722, 1 636, 1 5 68 cnT1 · 400 MHz! H NMR (CDC13) δ 0. 88 (6H? T, J = 6. 6 Hz), 1. 26 (30H, bs), 1. 40 (3H, s), 1. 4 Bu 1. 68 (7H, m, including 3H, s, at δ 200413400 1. 49 ppm), 2.56 (2H, t, J = 6. 3 Hz), 3. 23 (1H, m), 3. 38-3. 50 (4 H, m, including 2 H, s, at δ 3 · 4 1 ppm), 3 · 6 6-3 · 8 2 (3 H, m), 3 · 9 2 (1H, m), 4 · 05 (1H, m), 4. 30 (1H, m), 4. 47 (1H, d, J = 8. 1 Hz), 4_95 (1H, m), 5. 14-5. 27 (2H, m), 5. 84 (1H, m) · FABMS (cation) m / z, 623 [M_H] +, 647 [M + Na] + · (2) allyl 3-O-decyl-2 -O- (3-oxy Tetradecylfluorenyl) -β-D-glucopyranoside (Project A a5) The compound obtained in (1) (2. 37g, 3. 79mmol), reacted according to the method of Example 1 (5) to obtain the title compound (1. 27 g, yield 59%). Thai IR vmax (film) 3284 (br), 292 1, 2852, 1752, 1720, 1 649, 1632 cm'1. 400 MHz lU NMR (CDC13) δ 0. 88 (6H, t, J = 6. 6 Hz), 1. 26 (30H, bs), 1.5 Bu 1. 63 (4H, m), 2. 07 (1H, bs, OH), 2. 52-2. 57 (2H, m), 3. 20 (1H, d, J = 2. 9 Hz), 3. 45 (1H, s), 3. 35-3. 41 (2H, m), 3. 5 8-3. 68 (3 H, m), 3. 80 (1H, m), 3. 91 (1H, m), 4. 07 (1H, m), 4. 31 (1 H, m), 4 · 4 6 (1 H, d, J = 8. 1 Hz), 4. 94 (1H, m), 5. 16-5. 28 (2H, m), 5. 86 (1H, m). · FABMS (cation) m / z, 5 8 3 [MH] +, 607 [M + Na] + · (3) (E) — 1 —propanyl 3 — O —decyl — 2 — O — (3 —Oxytetradecanyl) -β-D-glucopyranoside (Project A a6) The compound (1 10 mg) obtained in (2) was reacted according to the method of Example 1 (6) to obtain the title. Compound (110 mg, 100% yield). IR vmax (film) 3500-3200, 2922, 2 8 5 3, 1 745, 1 720, 1682 (w), 1 648 (w), 1 630 (w) cm " 1. -209-200413400 400 MHz lR NMR (CDC13) δ 0. 88 (6H, t, J = 6. 6 Hz), 1. 26 (30H, bs), 1. 51-1. 62 (7H, m, including 3H, d, J II 5. 9 Hz, at δ 1. 54 ppm), 2. 02 (1H, bs, OH), 2. 52-2. 58 (2H, m), 3.19 (1H, d, J = 10. 3 Hz), 3. 3 6-3. 48 (3 H, m, including 2 H, s, at δ 1. 45 ppm), 3. 57_3 · 70 (3H, m), 3.81 (1H, m), 3. 93 (1H, m), 4. 62 (1H, d, J = 8. 1 Hz), 4. 99 (1H, m), 5. 10 (1H, m), 6. 16 (1H, dd, J = 1. 5, 12. 5 Hz). FABMS (cation) m / z, 607 [M + Na] +. (4) (E) — 1 monopropenyl 6 — 0 — (third butyl dimethylsilyl) — 3 — 0 — decyl — 2 — 0 — (3-oxytetradecanyl) — β — D — glucopyranoside (Project A a7) The compound obtained in (3) (1 17 mg, 0 · 18 8 mm ο 1) was reacted according to the method of Example 1 (7) to obtain the title compound. (1 15mg, yield 87%) 0 IR vmax (film) 3507 (br), 2927, 2856, 1754, 1 682 (w), 1663 (w), 1621 (w), 1465 cm'1. 400 MHz lH NMR (CDC13) δ 0. 08 (6H, s), 0. ******. 91 (15H, m, including 9 H, s, a t δ 0 · 9 0 p p m), 1 · 2 5 (3 0 H, b s), 1. 5 0 -1. 6 1 (5 H, m), 2. 55-2. 58 (2H, m), 3. 12-3. 20 (1H, m), 3. 36-3. 46 (3H, m), 3. 54-3. 73 (3H, m), 3. 83-3. 93 (2H, m), 4. 57 (1H? D, J = 8. 8 Hz), 4. 98 (1H, m), 5. 08 (1H, m), 6. 14 (1H, d, J = 10. 7 Hz). FABMS (cation) m / z, 697 [M-H] +, 721 [M + Na] + (added Nal). -210-200413400 (5) (E) — 1 propranyl group 4 — 0 — propoxyfluorenyl — 6 — 0 — (third butyldimethylsilyl) — 3 — 0 — decyl — 2 — 〇 — (3-oxytetradecanyl) -β-D-glucopyranoside (Project A a8) The compound obtained in (4) (950mg, 1. 3 60 mmol), and reacted according to the method of Example 1 (8) to obtain the title compound (720 mg, yield 68%) as an oily substance. IR Vmax (film) 2927, 2856, 1 75 8, 1 682 (w), 1 664 (W), 1628 (w), 1464 cm'1. 400 MHz] H NMR (CDC13) δ 0. 04 (6H, s), 0. ******. 90 (15H, m, including 9H, s, at δ 0. 88 ppm), 1 · 2 6 (3 OH, b s), 1. 42-1. 60 (7H, m, including 3 H, d, J = 7 · 3 H z, a t δ 1. 52 ppm), 2. 54 (2H, t, J = 7. 3 Hz), 3. 19 (1H, d, J = 8. 8 Hz), 3. 43 (1H, s), 3. 47-3. 57 (4H, m), 3. 72-3. 73 (2H, m), 4. 57 (1H, d, J = 8. 1 Hz), 4. 61-4. 65 (2H, m), 4. 78 (lH, t, J = 9. 5Hz), 4. 97-5. 14 (2H, m), 5. 27-5. 39 (2H, m), 5. 92 (1H, m), 6. 16 (1H, dd, J = 1. 5, 12. 5 Hz). FABMS (cation) m / z, 805 [M + Na] +. (6) 4-0-allyloxycarbonyl-3-0-decyl-2-0- (3-oxytetradecanyl) -D-glucopyranose (Section A a 10) will ( 5) The obtained compound (2. 98g, 3. 95 mmol) and reacted according to the method of Example 10 (6) to obtain the title compound (2.16 g, yield 58%). IR vmax (membrane) 2430 (br), 2925, 2855, 1 7 54, 1719, 1 650 (w), 14 6 6 cm " 1. 400 MHz! H NMR (CDC13) δ 0. 88 (6H, t, J = 6. 6 Hz), 1. 26 -211-200413400 (30H, bs), 1. 45- 1. 70 (4H, m), 2. 50-2. 57 (2H, m), 3. 47-3. 80 (7H, m), 3. 90 (1H, d, J = 9. 5 Hz), 4. 02 (1H, m), 4.66 (2H, d, J = 5. 9 Hz), 4. 76-4. 8 8 (1. 5H, m), 5. 29-5. 40 (2H, m), 5. 49 (0. 5H, bs), 5. 93 (1H, m). FABMS (cation) m / z, 3 69, 611, 651 [M + Na] +. HRFABMS C34H60O10Na Calculated 値: 65 1. 4085. Found 値: 65 1. 4052. (7) 4-O—canyloxy-based 3—O—decyl-6—〇— {2-deoxy-4—0—diallylphosphonic acid—3—0— [(R) — 3-methoxydecyl] -6-0-methyl-2-[(2,2,2-trichloroethoxycarbonyl) amino] -β-D-glucopyranosyl 2--0- -Oxytetradecanyl)-D-glucopyranose (CCl project) The compound of (6) (64 1mg, 1. 0 19 mmol) and the imidate used in Example 1 (10) (877 mg, 1. 04mmol), reacted according to the method of Example 1 (10), to obtain the title compound (1. 30 g, yield 97%). IR vmax (film) 3500-3200, 2927, 2856, 1 753, 1737, 1721 (shoulder) cm " 1. 400 MHz lE NMR (CDC13) δ 0. 88 (9H, t, J = 6. 6 Hz), 1. 26 (40H, bs), 1. 40- 1. 50 (4H, m), 1. 57- 1. 63 (2H, m), 1.70-1.78 (2H, m), 2. 5 Bu 2.55 (2H, m), 3. 35-3. 8 8 (24H, m, including 2 3H, s, at δ 3. 27 and 3. 39 ppm), 4. 18-4. 30 (2H, m), 4. 55 (0. 5H, m), 5. 25 -5. 43 (6. 5H, m), 5. 89-5. 99 (3H, m), 6. 65 (1H, br). FABMS (cation) m / z, 1 330 [M + Na, 35C1] +, 1 3 3 2. HRFABMS C61H 1 0 5 3 5 Cl3NO20PNa Calculation 値: 1 3 30. 593 1. Found -212-200413400 値: 1330. 5928. (8) 4-0 -Allyloxycarbonyl- 3-0 -decyl-6-0-{2-deoxy-4-10-diallylphosphonic acid-3-0-[(R) — 3 —Methoxydecyl] —6--0—methyl-2 — [(Z) —11— (octadecenyl) amino] —β-D-glucopyranosyl} —2_0— (3 —Oxytetradecanyl) -D-pyranobiose (Project C c2) The compound (1) 290g, 〇. 985 mmol) and reacted according to the method of Example 1 (11) to obtain the title compound (75 6 mg, yield 55%) as an oil. φ IR vmax (film) 3305 (br), 2926, 2856, 1 755, 1 652, 1 543, 1465 cm’1 · 400 MHz lU NMR (CDC13) δ 0. 88 (12H, m), 1. 26 (60H, bs), 1. 40-1. 80 (10H, m), 2. 01-2. 02 (4H, m), 2. 16-2. 22 (2H, m), 2. 52-2. 59 (2H, m), 3. 04-4. 37 (25H, m, including 2 3H, s, at δ 3. 27 and 3. 39 ppm), 4. 54-4. 78 (7H, m), 5. 00m (0. 5 H, s), 5. 23-5. 52 (8. 5H, m), 5. 86-5. 98 (3H, m), 6. 09 (1H, d, J = 7. 3 Hz, NH). Call FABMS (cation) m / z, 1420 [M + Na] +. HRFABMS, C76H136N019PNa Calculation: 1420. 9342. Found 値 1420. 9347. (9) Dicanyl phosphono 4-10-canyl oxy group — 3 — 0 — decyl — 6 — 0 — {2 —deoxy-4 — 0 — diallylphosphonic acid — 3 — 0 — [(R) —3-methoxydecyl] —6--0—methyl—2 — [(Z) —11— (octadecenyl) amino] —β-D-glucopyranose Radical}-2-0 — (3-oxo-213-200413400-tetradecanylidene) -α-D-glucopyranoside (° ^ -body) and diallylphosphonic acid group 4-0-allyloxy Carbonyl- 3-0-decyl-6- 0-{2 -deoxy-4-0-diallylphosphonic acid -3-0-[(R)-3 -methoxydecyl]-6-0 —Methyl-2 — [(Z) —11- (octadecenyl) amino] -β-D-glucopyranosyl} —2—0— (3-oxytetradecanyl) ) One β-D-glucopyranoside (β-body) (Project Ca4) The compound obtained in (8) (743 mg, 0. 531 mmol), and reacted according to the method of Example 1 (13) to obtain the title compound as the cx form (166 mg, yield 20%) and the beta form (185 mg, yield 22%) as an oil. Alpha body ·· IR vmax (film) 3306, 3086 (w), 2926, 2856, 1 759, 1721, 1 666, 1 548 cm-1. 400 MHz lH NMR (CDC13) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 26 (60H, bs), 1. 46- 1. 73 (10H, m), 2. 00-2. 05 (4H, m), 2. 21-2 · 24 (2H, m), 2.53 (2H, t, J = 7. 7 Hz), 3. 24-3. 79 (1 9H, m, including 2 3H, s, at 3. 28 and 3 · 38 ppm), 3.88-3 · 98 (2H, m), 4.08 (1H, m), 4. 27 (1H, m), 4. 54-4. 65 (1 1H, m), 4. 75-4. 83 (2H, m), 5. 24-5. 42 (12H, m), 5. 80 (1H, dd, J = 3. 7, 6. 6 Hz), 5. 89-5. 99 (5H, m), 6. 54 (1H, d, J = 7. 3 Hz, NH). FABMS (cation) m / z, 1 558 [M + H] +, 1 5 80 [M + Na] +. HRFABMS, C82H145N022P2Na Calculated 値: 1 5 8 0 · 9 6 3 2 Found 値: 1580. 9617. Beta body: IR vmax (membrane) 3309, 308 6 (w), 2926, 2856, 1 759, 1722, 1 669, -214-200413400 1 550 cm'1. 400 MHz] H NMR (CDC13) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 26 (60H, bs), 1. 38- 1. 70 (1 0H, m), 2. 00-2. 04 (4H, m), 2. 21-2 · 23 (2H, m), 2.53 (2H, t, J = 7. 4 Hz), 3. 2 Bu 3.79 (21H, m, including 2 3H, s, at 3. 27 and 3. 38 ppm), 3. 98 (1H, m), 4. 27 (1H, m), 4. 46-4. 72 (12H, m), 5. 00-5. 09 (2H, m), 5. 23-5. 42 (1 2H, m), 5. 85-5. 98 (5H, m), 7.35 (1H, d, J = 9. 5 Hz, NH). FABMS (cation) m / z, 1 580 [M + Na] 'HRFABMS, C82H145N022P2Na Calculated 値: 1 580. 9632. Found 値: 1580. 9650. (10) Squamate 3—O—decyl—6—O-{2 —deoxy—3 — 〇 — [(R) — 3 —methoxydecyl] — 6 — 0 —methyl — 2 — [ (Z) —11— (octadecenyl) amino] -4—10—phosphonic acid group—β-D-glucopyranosyl} —2—O— (3-oxytetradecane Group) a-D-glucopyranoside (Project C a5) The compound (9) obtained in (9) α form (178 mg, 0. 114 mmol) and reacted according to the method of Example 1 (14) to obtain the title compound (89 mg, yield 59%). IR vmax (KBr) 3286 (br), 2925, 2854, 1747, 1717, 1 630, 15 5 1, 1,466 cm " 1. 400 MHz NMR (C D C13-C D 3 〇 D, 5: 1) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 27 (60H, bs), 1. 40-1. 75 (10H, m), 2. 00-2. 04 (4H, m), 2. 22-2. 35 (2. 5H, m), 2. 58 (1. 5H, t, J = 7. 3 Hz), 3. 24-4. 10 (24H, m), 4. 69 (1H, m), 4. 76 (1H, d, J = 8. 1 Hz), -215-200413400 5. 3 3 -5. 3 6 (2H, m), 5. 67 (1H, m). FABMS (anion) m / z, 1312 [M-H] ·· C66H125N〇2〇P2 Analytical calculation 値: C, 60. 30; H, 9. 58; N, 1. 07; P, 4. 7 1. Measured 値: C, 5 9 · 8 7; Η, 9 · 6 4; N, 1 · 4 1; P, 4. 6 5 · [Example 22] Glucosanoic acid group 3-0-decyl 6-0-{2-deoxy-3-0-[(R)-3-methoxydecyl]-6-0-methyl 2-[(Z) —11- (octadecenyl) amino]-4-10-phosphonic acid-β-D-glucopyranosyl} -2-0- (3-oxo Tetradecyl fluorenyl) -β-D-glucopyranoside (Project C a 5) The compound β-body (160mg, 0. 0) obtained in Example 21 (9) 103 mmol) and reacted according to the method of Example 1 (14) to obtain the title compound (97 mg, yield 72%) ° IR vmax (KBr) 3287 (br), 2925, 2854, 1 746, 1717, 1 629, 1554, 1466 cm " 1. 400 MHz! H NMR (CDCI3-CD3OD, 5: 1) δ 0. 88 (12H, t, J = 6. 6 Hz), 1. 26 (60H, bs), 1. 40-1. 73 (10H, m), 2. 01-2. 02 (4H, m), 2. 20-2. 37 (2. 5H, m), 2. 58 (1. 5H, t, J = 7. 3 Hz), 3. 30-3. 82 (2 1 H, m, including 2 3H, s at 3. 30 and 3. 41 ppm), 4. 01-4. 05 (3H, m), 4. 88-4. 94 (2H, m), 5. 05 (1H, m), 5. 33-5. 36 (2H, m). FABMS (anion) m / z, 1312 [Μ-ΗΓ. C66H 〖25N〇2 () p2 Analysis and calculation 値: C, 60 · 30; H, 9. 58; N, 1. 07; P, 4. 7 Measured 値: C, 59. 93; H, 9. 75; N, 1. 29; P, 4. 58. -216-200413400 [Test Example 1] Inhibition test on human whole blood T N F α production (in vitro) This test can be performed according to the method of H a r t m a η (D. A. Hartman, S. J. Ochalskiand R. P. Carlson; The effects of antiinflammatory and antiallergic drugs on cytokine release after stimulation of human whole blood by lipopolysaccharide and zymosan A: Inflamm. Res., 44, 269 (1995)). Peripheral blood was collected from healthy volunteers in the presence of heparin. Inject 3 60 mL of whole blood into a 96-well plate containing 20 jiL of dimethicone solution of the test compound in advance, and then add a stimulant lipopolysaccharide (LPS) (from coliform 〇26: B 6, Difco) (final concentration l Ng / mL) 20 pL, thoroughly mixed, and cultured at 37 ° C and 5% C02 for 6 hours. After the end of the culture, the reaction was stopped by cooling to 4 ° C, that is, centrifugation at 2000 r p m for 15 minutes, and the supernatant plasma was separated and recovered. The released TN Fa in plasma was measured by an enzyme immunoassay (E L I S A) kit (B i 0 s 0 u r c e). The inhibition rate was determined from the amount of cytokinin produced in the presence or absence of the test compound. Based on these average inhibition rates, I C 5q 依 was calculated by the minimum automultiplication method. The results are shown below. [Table 1] Test compound IC 5G (nM) ^ 5 6 7-9 IX 2 3 4 5 6 V 8 IX 11 1- 1- Λ \ — 户〆_ rflΛ \-4Λ Hehehehehehehehehehehehehehehehehehehehe 16 0 • 3 1 0 • 3 7 0 • 019 0 • 20 1 2. 2 0 • 63 3. 2 0. 6 -217-200413400 [Test Example 2] Inhibition test of human whole blood T N F α (in vitro) According to the method of Test Example 1, c 5 () 値 of the test compound can be obtained. Using the compound described in U.S. Patent No. 593 593 8 as a comparative compound, c 5Q 値 was obtained in the same manner as the test compound. The structure of the comparative compound is as follows: 〇Me

〔表2〕試驗化合物 ^- ——---- I C 5〇(nM) 化合物12 — 0.1 化合物13 0.3 化合物1 6 0.5 化合物1 7 0.9 化合物18 1.4 化合物19 0.3 比較化合物 — — 2.0 ----- _[Table 2] Test compound ^----- IC 5〇 (nM) Compound 12 — 0.1 Compound 13 0.3 Compound 1 6 0.5 Compound 1 7 0.9 Compound 18 1.4 Compound 19 0.3 Comparative compound — 2.0 2.0 -_

-218 - 200413400 〔試驗例3〕對人全血T N F α産生之抑制試驗（活體外）依試驗例2之方法，可得試驗化合物之I C 5G値。使用與試驗例2相同之比較化合物。本試驗例結果示於表3。〔表3〕試驗化合物 I C 5〇(ηΜ) 化合物1 3 0.19 • 化合物14 0.14 化合物1 5 0.18 化合物2 1 0.20 比較化合物 0.30 〔試驗例4〕對小白鼠T N F α産生之抑制活性試驗（活體內） _ 本試驗可依Υ · E n d 〇之方法（British Journalof Pharmacology 128，5- 1 2 ( 1 999))來進行。使用已知對脂多糖（LPS)有强感受性之C3H/HeN小白鼠 (雄，7週齢），每群使用5隻。將半乳糖胺（GalN， lg/5ml)及LPS ( 0.05mg/5ml )各以生理食鹽水溶解後，等量混和而調製GaULPS溶液。所調製之GalN_LPS溶液以 10ml/kg之比例自尾静脈内注射。將試驗化合物溶在0.1% -219 - 200413400 三乙胺水溶液，於注射GalN.LPS溶液同時以10ml/kg之比例自尾静脈内注射。注射GalN.LPS溶液1小時後以乙醚麻醉，採取小白鼠下行大静脈之血液，分離血漿。血漿中 TNFa產生量以市售TNFcx酵素免疫測定套組測定。試驗化合物之TNFa産生抑制活性，可相對於注射GalN.LPS所産生TNFa而算出抑制率。試驗結果示於表4。〔表4〕試驗化合物對注射GalN.LPS所産生TNFa之抑制率（％) 化合物 14 91.8 化合物 15 85.3 化合物 17 88.8 化合物 18 90.1 化合物 21 84.8 比較化合物 75.4 〔試驗例5〕對小白鼠致死之救命試驗（活體內）本試驗可依Η · 丁 a k a d a方法（The Journal of Infectious Diseases 162，428-434 (1990))來進行。注射GalN^LPS溶液72小時後観察小白鼠之生死，算出生存率。所使用小白鼠，週齢，性別，GalN · LPS及化合物 -220 - 200413400 投予液之調製法，投予途徑及計時等可依試驗例4方法來進行。本試驗每群使用1 〇隻小白鼠。試驗結果示於表5。-218-200413400 [Test Example 3] Inhibition test of human whole blood T N F α (in vitro) According to the method of Test Example 2, I C 5G 値 of the test compound can be obtained. The same comparative compound as in Test Example 2 was used. The results of this test example are shown in Table 3. [Table 3] Test compound IC 50 (ηΜ) Compound 1 3 0.19 • Compound 14 0.14 Compound 1 5 0.18 Compound 2 1 0.20 Comparative compound 0.30 [Test Example 4] Inhibitory activity test on TNF α production in mice (in vivo) _ This test can be performed in accordance with the method of End 〇 (British Journal of Pharmacology 128, 5- 12 (1 999)). C3H / HeN mice (male, 7 weeks old), known to have a strong sensitivity to lipopolysaccharide (LPS), were used in groups of five. Each of galactosamine (GalN, lg / 5ml) and LPS (0.05mg / 5ml) was dissolved in physiological saline, and they were mixed in equal amounts to prepare a GaULPS solution. The prepared GalN_LPS solution was injected into the tail vein at a ratio of 10 ml / kg. The test compound was dissolved in a 0.1% -219-200413400 triethylamine aqueous solution and injected into the GalN.LPS solution at the same time as a 10 ml / kg ratio from the tail vein. One hour after the injection of the GalN.LPS solution, anesthesia was performed with ether, and blood from the descending large vein of the mouse was collected to separate the plasma. The amount of TNFa produced in plasma was measured using a commercially available TNFcx enzyme immunoassay kit. The inhibitory activity of the test compound on TNFa production can be calculated with respect to the TNFa production by injection of GalN.LPS. The test results are shown in Table 4. [Table 4] Inhibition rate (%) of test compound on TNFa produced by injection of GalN.LPS Compound 14 91.8 Compound 15 85.3 Compound 17 88.8 Compound 18 90.1 Compound 21 84.8 Comparative Compound 75.4 [Test Example 5] Life-saving test for mice (In vivo) This test can be performed in accordance with the Ding akada method (The Journal of Infectious Diseases 162, 428-434 (1990)). 72 hours after the injection of GalN ^ LPS solution, the life and death of mice were observed, and the survival rate was calculated. The preparation method, administration route and timing of the used mice, Zhou Yan, sex, GalN · LPS and compound -220-200413400 administration solution can be performed according to the method of Test Example 4. In this experiment, 10 mice were used in each group. The test results are shown in Table 5.

7 2小時後小白鼠之生存率（％) 投予量（mg/kg) 試驗化合物：化合物1 3 化合物14 0 10 10 0.3 20 20 1 50 50 3 60 50 10 80 70 産業上之利用可能性本發明之右糖葡萄糖脂肪質A同類物具有優異噬菌體活性抑制作，可作爲抗炎症劑，抗自體免疫疾病劑，免疫抑制劑，冠狀動脈旁路形成術後預後改善劑或抗敗血症劑。 -221 -7 Survival rate of mice after 2 hours (%) Dosage (mg / kg) Test compound: Compound 1 3 Compound 14 0 10 10 0.3 20 20 1 50 50 3 60 50 10 80 70 Industrial utilization possibility The dextrose glucolipid A of the invention has excellent phage activity inhibitory action, and can be used as an anti-inflammatory agent, an anti-autoimmune disease agent, an immunosuppressive agent, a prognostic improvement agent or an antiseptic agent after coronary artery bypass formation. -221-

Claims

200413400 Scope of patent application 1 · A compound of the following formula or its pharmacologically acceptable salt:

[In the formula, Q is an oxygen atom, Ci—c3 alkylene, group —O-Alk- or —O-Alk-O- (but Aik is C 1 —C 3 alkylene), R1, R2, and R4 Are the same or different, each is a hydrogen atom, and may have a C 1 -c 2 alkyl group substituted with one or more groups selected from the following substituent group A, and may be substituted with one or more groups selected from the following substituent group A The C2-C20 alkenyl group may have a C 2 -C 2Q alkynyl group substituted with one or more groups selected from the following substituent group A, and may be substituted with one or more groups selected from the following substituent group A (:! A C 2G alkylfluorenyl group may have a C3-C 2G alkenyl group substituted with one or more groups selected from the following substituent group A or C 3 — substituted with one or more groups selected from the following substituent group A C 2o alkynyl, R 3 is a C 1 -C 2G alkyl group which may be substituted with one or more groups selected from the following substituent group A, and may be substituted with one or more groups selected from the following substituent group A The C3-C 2G alkenyl group may have a C 3-C 20 alkynyl group substituted with one or more groups selected from the following substituent group A, R 5 is a hydrogen atom, a halogen atom, and the hydroxyl group may be Ci One C6 is too oxy, can be aerobic C2-C6 alkoxy or oxo-2-C6 alkynyloxy, the substituent group A is a halogen atom, hydroxy, oxy, oxyC] _ C2Q courtyard oxy, (Cl — C2G oxo) Cl-C2G oxo '-222-20 焼 oxy} Cl — C2. Gasoyl radicals may be C2-C2, which may be oxygen, and C2_C2, which may be oxygen. The alkynyloxy group may have a C! -C20 alkylalkoxy group, and may have a C3-Cm allenyloxy group, and may have an oxygen group (: 3-C2. An alkynyloxy group and Cl- C20 sulfonyl group] 2. If the compound or the pharmacologically acceptable salt of the first item of the patent application scope, R 1 is a C 4 -C 1S alkane or C which may have a substituent selected from the substituent group A 4-C 1 8 flammable radical. 3 · If the compound or the pharmacologically acceptable salt of the first scope of the patent application, R 1 is C 4 -C 18 which may have a substituent selected from the substituent group A. 4 · The compound or pharmacologically acceptable salt thereof according to item i of the patent application range, wherein R 1 is a c 8 -C! Salkyl 戌 C 8 -C 1 8 dilute group which may have a substituent selected from the substituent group A. 5 If the compound in the scope of patent application item 1 or The pharmacologically tolerable salt thereof, wherein R 1 is a C 8-c 18 alkyl group which may have a substituent selected from the substituent group A. 6 · If the compound or the pharmacologically tolerable salt of item 1 of the patent application scope, R 1 is an unsubstituted or C 1Q — C 18 alkyl or C IQ — C 18 alkenyl group substituted by a hydroxy group or an oxy group selected from the substituent group A. 7. If the compound or pharmacologically acceptable salt of item 1 in the patent application 5R, it is preferred that R 1 is unsubstituted or substituted with a hydroxyl group or an oxy group selected from substituent group A as a C i — ci 8 alkane base. 8) The compound or pharmacologically acceptable salt thereof according to item 1 of the scope of patent application, wherein R 1 is unsubstituted or substituted with hydroxy or oxy selected from substituent group A as decyl, dodecyl, and fourteen Base, dodecenyl or tetradecyl 200413400 alkenyl. 9 · If the compound or pharmacologically acceptable salt of the item 1 in the scope of the patent application, ψ R 1 is unsubstituted or substituted with a hydroxy or oxy group selected from the substituent group A as a decyl, dodecyl or ten Four bases. 10. The compound or pharmacologically acceptable salt thereof according to any one of the items 1 to 9 of the scope of patent application, wherein R 2 is C4-Ci8 or C4-Cl8 which may be substituted with a substituent selected from Substituent Group A. Too basic. 1 1 · A compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 9, wherein R 2 is a C 4 -Ci 8 fluorenyl group which may be substituted with a substituent selected from Substituent Group A. 1 2 The compound or pharmacologically acceptable salt as described in any one of items 1 to 9 of the patent scope of claim I, wherein R 2 is 008-Ci8, which may be substituted with a substituent selected from substituent group A, or C8—C18 alkenyl. 1 3. The compound according to any one of claims 1 to 9 or a pharmacologically acceptable salt thereof, wherein R 2 is a Ci8 compound which may be substituted with a substituent selected from the substituent group A. 14 · The compound or pharmacologically acceptable salt thereof according to any one of claims 1 to 9, wherein R 2 is unsubstituted or a C1G-Cls alkyl group substituted with a hydroxy group selected from the substituent group A as a substituent Or Cl ()-C18 alkenyl. 1 5. The compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 9 in the scope of patent application, wherein R 2 is unsubstituted or substituted with a hydroxyl group selected from the substituent group A C 1 0 — C ] 8 Yuan Ji. 16 · The compound or pharmacologically acceptable salt thereof according to any one of items 1 to 9 of the patent scope, wherein R 2 is unsubstituted or has a hydroxyl group selected from the substituent group A-224 ^ 200413400 as a substituent substitution Decyl, ten to its, ms ^ r, to tetradecyl, 5 dodecenyl or 7 to tetradecenyl. 17. If applying for a patent, any one of the ~ 9 compounds or their pharmacologically acceptable salts 'wherein R2 is unsubstituted or substituted with a hydroxy group selected from substituent group a as a decyl' dodecyl or ten Four bases. A compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 9, wherein R2 is unsubstituted ^. A Ci8 alkyl. 19. The compound or pharmacologically acceptable salt thereof according to any one of items i to 9 of the scope of patent application, wherein R2 is unsubstituted decyl, dodecyl or tetradecyl. 2 0. The compound or pharmacologically acceptable salt thereof according to any one of claims 1 to 19 in the scope of application of rP3, wherein R3 is an unsubstituted c 8-c 18 alkylfluorenyl group. 2 1. The compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 9 in the scope of the patent application, wherein R3 is an unsubstituted ClQ-Cl8 alkylfluorenyl group. 22. The compound or pharmacologically acceptable salt thereof according to any one of claims 1 to 9 in the scope of the application for a patent, wherein R3 is formamyl, ethenyl or propionyl. 2 3 · The compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 19 in the scope of application for a patent, wherein R3 is methylamidino or ethylamido. 24. The compound or pharmacologically acceptable salt thereof according to any one of claims 1 to 19, wherein R 4 is C 4 -Ci 8 or C 4-which may be substituted with a substituent selected from Substituent Group A Cl8 burns base. 2 5 · The compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 19 in the scope of patent application, wherein R 4 is a c 4 -C i 8 alkyl group which may be substituted with a substituent selected from the substituent group A . 2 6. The compound according to any one of claims 1 to 19 or its pharmacology -225-200413400 allowable salt 'wherein R 4 is a C8-Ci8 compound which may be substituted with a substituent selected from substituent group A Or C8-Cl8 dilute. 27. A compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 19, wherein R 4 is a C 8 -C i 8 alkyl group which may be substituted with a substituent selected from the substituent group A. 28. The compound or pharmacologically acceptable salt thereof according to any one of claims 1 to 19 in the scope of application for a patent, wherein R4 is a fluorine atom selected from the substituent group A, and is unsubstituted C12-C14 oxygen , Unsubstituted Ci2-Cl4 canoxy 'unsubstituted cnc MU or oxo or unsubstituted C c 14 substituted oxo substituted C 10 — C is or C IQ — C 18 · A compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 19, wherein R4 is a fluorine atom selected from the substituent group A, and is unsubstituted by a group, and the unsubstituted c12-C14 alkoxy group is unsubstituted c12-c14 alkoxy, unsubstituted C u-C alkoxy or C 1 Q-C i 8 substituted with unsubstituted c ^ -c 14 bridge oxy. 3 0. The compound or pharmacologically acceptable salt thereof according to any one of the items i to i 9 in the scope of application for patent, wherein R4 is a fluorine atom selected from a substituent group, a hydroxyl group, an unsubstituted Cc M alkoxy group or an unsubstituted c C 1 Q-C 1 8 alkyl substituted with a substituent of 12-c 14 alkylalkoxy. 31. If the compound or any of its pharmacologically acceptable salts in any one of items i to 19 of the scope of application for a patent, wherein R4 is a fluorine atom selected from the substituent group 厶, a hydroxyl group, an unsubstituted c C M alkenyloxy group or an unsubstituted C 12-c 14 alkyleneoxy substituted C! Q-C i 8 alkyl. -226-413400 As described in Shenyang Patent Scope 1 ~; [A compound of any one of 9 or its pharmacologically acceptable salt 'wherein R4 is a fluorine atom selected from the substituent group A, and the hydroxyl group is unsubstituted (:! 2 -CM alkoxy or unsubstituted c12-c18 alkenyloxy substituted c 1G-C 18 alkyl. 3 3 'As claimed in any of claims 1 to 19 of the patent scope of 1 or 19 Pharmacologically tolerable salts, in which R4 is a C 1Q ~ ◦ 18 group substituted with a fluorine atom selected from substituent group A, a hydroxyl group or a substituent substituted with an unsubstituted C 12 -C 14 alkoxy group. The compound according to any one of 1 to 19 or a pharmacologically acceptable salt thereof, wherein R4 is a fluorine atom selected from the substituent group A and substituted with a substituent of the group 'unsubstituted C i 2 -C! 4 alkenyloxy C! 〇 ~ C i 8 Yuanji. 3 5 · As a compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 19, wherein R4 is a dodecyloxy group selected from the substituent group A , Tetradecyloxy, 5-dodecyloxy, 7-tetradecyloxy, 12-membered Moxy, 14-membered fluorenyloxy, 5-dodecyloxy or 7 ~ 10 Tetraene Substituent for decyl, dodecyl, tetradecyl, 5-dodecenyl, or 7-tetradecenyl. 3 6 · As in any one of claims 1 to 19 of the scope of patent application Compound or a pharmacologically acceptable salt thereof, wherein R4 has a dodecyloxy group, a tetradecyloxy group, a 5-dodecenyloxy group, a 7-tetradecenyloxy group, and a dodecane group selected from the substituent group A Fluorenyloxy, tetradecylfluorenyloxy, 5-dodecenyloxy or 7-tetradectenyloxy substituted decyl'dodecyl or tetradecyl. 3 7. If applying for a patent The compound according to any one of the items 1 to 19 or its pharmacological-227-200413400 permissible salt, wherein R4 is a dodecyloxy group, a tetradecyloxy group, a dodecylfluorenyloxy group selected from the substituent group A, or A decyl, dodecyl or tetradecyl group substituted by a substituent of a tetradecylfluorenyloxy group. 3 8. The compound or a pharmacologically acceptable salt thereof according to any one of claims 1 to 19 of the scope of application for a patent, wherein R4 is Decane substituted with a substituent selected from 5-^ dicarbenyloxy, 7-tetradecenyloxy, 5-11-undecyloxy or 7-tetradecenyloxy of substituent group A Base, twelve base or fourteen base. 3 9. The compound according to any one of claims 1 to 19 or a pharmacologically acceptable salt thereof, wherein R4 is a dodecyloxy group, a tetradecyloxy group, a 5-dodecyl group selected from the substituent group A Decenyl, dodecyl or tetradecyl substituted with alkenyloxy or 7-tetradecene alkenyloxy. 4 0. A compound as claimed in any one of claims 1 to 19 or its pharmacology Permissible salts, where R4 is decyl, dodecyl or tetradecyl substituted with a substituent selected from dodecyloxy or tetradecyloxy of substituent group A. 4 1 · As for the range of patent applications 1 ~ 1 The compound according to any one of 9 items or a pharmacologically acceptable salt thereof, wherein R4 is a decyl group substituted with a substituent selected from 5-dodecyl; oxy group or 7-tetradecyloxy group of substituent group A, Twelve or fourteen. 4 2. The compound or pharmacologically acceptable salt thereof according to any one of claims 1 to 41 in the scope of application for a patent, wherein R5 is a halogen atom, and is substituted or unsubstituted. 43. The compound or the pharmacologically acceptable salt thereof according to any one of claims 1 to 41, wherein R5 is a fluorine atom, a hydroxyl group, or a methoxy group. 4 4 · The compound or any of the pharmacologically acceptable compounds in any one of items 1 to 4 of the scope of the patent application -228-200413400 Allowable salt, where Q is an oxygen atom. 45. The compound according to any one of claims 1 to 43 or a pharmacologically acceptable salt thereof, wherein Q is ethyl phosphonate. 4 6. The compound or any of its pharmacologically acceptable salts according to any one of claims 1 to 45 in the scope of patent application, in which the dextran glucose 1 position is the ex position. 47. As in the scope of application for patents Nos. 1 to 46, which are the following compounds or their pharmacologically acceptable salts, the phosphonic acid group 6-〇- [2-deoxy-4-◦ monophosphonic acid group 3-0-[( R) — 3 —methoxydecyl] —6—〇-methyl—2 — [(Z) —11— (octadecenyl) amino] —β-D-pyranosyl] — 3-0-decyl-2-0-0 [(R) -3-Zen tetradecyl] -β-D-glucopyranoside, phosphonic acid group 6-0- [2-deoxy-4 4-0 Monophosphonic acid group 3—0 — [(R) —3—methoxydecyl] —6—0—methyl—2 — [(Z) —11— (octadecenyl) amino] — β-D -pyranoglucosyl] -3-0-decyl-2-0-[(R)-3-hydroxytetradecyl]-α-D-glucopyranoside, phosphonic acid group 6- 〇一 [2-Deoxy-4—〇-phosphonic acid group 3—0-fluorene: (R) —3-methoxydecyl] 6-〇-methyl-2— [(Z) -11-1 (Octadecenyl) amino group] -β-D-glucopyranosyl] -3-0-10-yl-2-0-0 [ (R) 3-3-tetradecyl] -β-D-pyranoglucoside, phosphonic acid group 6-0- [2-deoxy-4 10-phosphonic acid group 3-0- [ R) —3-methoxydecyl] -6-〇-methyl-2 — [(Z-229-200413400) —11- (octadecylpyridinyl) amino] -β-D-glucopyranose Glycosyl]-3-12 dodecyl-2-0-[(R)-3-meridyl tetradecyl]-a-D-glucopyranoside, phosphonate 3-0-decyl-6 -〇- [2 -deoxy-4 -0-phosphonic acid group 3 -〇-[(R)-3-methoxydecyl]-6 -〇-methyl- 2- [(Z)-11- (Octadecenyl) amino group] -β-D-glucopyranosyl] -2-0-tetradecyl-a-D-glucopyranoside, phosphonic acid group 3-0-decyl-1 6-0- [2-deoxy-4-0-phosphonic acid group 3-0-[(R)-3-methoxydecyl] 6-〇-methyl- 2-[(Z) — 11 Mono (octadecenyl) amino group] -β-D-Π glucopyranosyl] -2-0-tetradecyl-β-D-D glucopyranose , Phosphonic acid group 2,3-Dioxoyl-12-yl-6-O- [2 -deoxy-4 10-phosphonic acid-3-O-[[R) -3-methoxydecyl] 6-〇-methyl-1 2-[(Z) -11- (octadecenyl) amino] -β-D-glucopyranosyl] -α-D-glucopyranoside, phosphine Acid group 2,3-dioxalyl-12-yl-6-one- [2-deoxy-4-0-phosphonic acid- 3-0-[(R) -3-methoxydecyl] -6 10-methyl-2-[(Z) —11- (octadecylpyridinyl) amino] -β-D-glucopyranosyl] -β-fluorene-pyranoglucoside, phosphonic acid group 2,3-dioxoyl-12-yl-6-Oi [2-deoxy-4-0-phosphonic acid group 3-Oi [(R)-3-methoxydecyl] -6- 〇-Methyl-2- [9- (octadecyl) amino] -mono-230-200413400 glucopyranosyl] -α-D-pyranoglucoside, phosphonate 2,3-dione 〇 Dodecyl-6—〇— [2-deoxy-4—10—phosphonic acid—3— ◦ — [(R) —3-methoxydecyl] —6—〇 Monomethyl 2- [9- (octadecyl) amino] -β-D-glucopyranosyl] -β-D-glucopyranoside, phosphonate 2,3-dione 101 Dodecyl-6-0- [2 -deoxy-4-0-phosphonic acid group 3-0-[(R) -3-methoxydecyl] -6-〇-methyl-2-[( Ε) — 9- (octadecenyl) amino] -β-D-glucopyranosyl] -a-D-glucopyranoside, phosphonate 3-0-decyl-6- 〇- [2-deoxy-4—0-phosphonic acid group—3—〇 — [(R) —3-methoxydecyl] —6—〇-methyl- 2 — [(E) — 9— ( Octadecenyl) amino]] β-D-glucopyranosyl] -2-0-tetradecyl-β-D-pyranoglucosamine, phosphono 3-10 One 6-0- [2-deoxy-4-0-phosphonic acid group 3-0-[(R) -3 3-methoxydecyl] 6-〇-methyl-1 2- [(Z) — 11- (octadecenyl) amino] -β · -D-glucopyranosyl] -2-0-tetradecyl-a-D-pyranoglucoside, Acid group 3-0 dodecyl-6-0- [2 -deoxy-4-0-phosphonic acid group 3-0-[(R) -3-methoxydecyl] -6-0-methyl 2-([Z) —11- (octadecenyl) amino] -β-D-D than glucosyl] -2-0-tetradecyl-β-D-laranyl Glycoside, -231-200413400 2- (phosphonooxy) ethyl 6-0- [2-deoxy-4-0-phosphono-3-0-[(R) -3-methoxydecyl] 6-0—methyl-1 2-[(Z) —11- (octadecenyl) amino] -β-D-glucopyranosyl] -3-0-dodecyl-2— 〇一 [(R) -3-tetradecyl] -a-D-pyranoglucoside, 2- (quanyloxy) ethyl 6-〇-1 [2-deoxy-4-〇-1 Glucosino- 3-0 — [(R) —3-methoxydecyl] -6-〇-methyl-1 2-[(Z) —11- (octadecenyl) amino] -β —D—glucopyranosyl] —3—120-dodecyl— 2—104-tetradecyl—α—D—glucopyranoside, 2- (phosphonic acid Ethyl) ethyl 6-0- [2-deoxy-4-0-phosphonic acid 3-3- ◦-[(R) -3-methoxydecyl] -6-〇-methyl-2 2- [( (Z)-11- (octadecylamino) amino] -β-D-glucopyranosyl] -2,3-dioxoyl-12-a-D-glucopyranoside, 2 — (Lincoloxy) ethyl 6-0 — [2-deoxy-4-10-phosphonic acid group 3—0-[(R) —3-methoxydecyl] -6-methyl group A 2-[(Z) -11- (octadecenyl) amino] -β-D-glucopyranosyl] -2,3-dioxalyl-12-pyridyl-β-D-pyridine Glucosinolate, 2-phosphonoethyl 6-0— [2-deoxy-3—0 — [(R) —3-methoxydecyl] —6—〇-methyl-2— [(Z) — 11- (octadecenyl) amino] -4 4- 10-phosphonic acid-β-D-glucopyranosyl] -2,3-dioxoyl-12-yl-a-D- Pyranose-232-200413400 glucoside, 3-mono (phosphonooxy) propyl 6 ~ 〇- {2-deoxy-3-〇-[(R) -3-methoxydecyl] -6 〇-methyl-2-[(Z) — 11- (octadecenylamino)] 4 ~ 〇-phosphono-β-D-glucopyranosyl} -2,3-dione 〇 ~ dodecyl-a-D-glucopyranoside, 3- (phosphono) propyl 6 ~ 〇- {2-deoxy-3--0-[(R) -3-methoxydecyl] 6 ~ 〇-methyl-2 [(z) — 11— (octadecenylamino)] ~ 4 ~ 〇-phosphono-β-D-glucopyranosyl} 2 '3-1 〇 ~ dodecyl-α-D-glucopyranosyl-6-〇- {2-deoxy-3 ~ 〇_ [(R) — 3-methoxydecyl] -6-〇-methyl-2 — [(Z) -n- (octadecenylamino)]-4-10 phosphono-β ~ D-glucopyranosyl} -2,3-dioxoyl-12 α-D-glucopyranose methyl dihydrogen phosphate, 6-〇- {2 -deoxy-3 ~ 〇- [(R)-3-methoxydecyl] -6- ◦ monomethyl-2 — [(Z) — 11- (octadecenylamino)] 4-10 phosphono-β-D- [l-glucopyranosyl} -2,3-di-11212 -Α-D-glucopyranose ethyl dihydrogen phosphate, 6 —〇一 {2-—Deoxy-3—〇 — [(R) — 3-methoxydecyl] -6—10—methyl—2 — [(Z) — 11— (octadecenylamino) )] 4-10 phosphono-β-D-glucopyranosyl} -2,3-dioxoyl-12-yl-D-pyranoglucosyl sulfonic acid, 2- ( Phosphonate) ethyl 6-0- {2-deoxy-3--0-[(R) -3-methoxydecyl] -6-〇-methyl-1 2-[(Z) — 11-- 233-200413400 (octadecenylamino)]-4-10-phosphono-β-D-glucopyranosyl}-2-0 tetradecyl-3-0-decyl-a- D -glucopyranoside, 6-〇- {2-deoxy-3-〇-[(R)-3-methoxydecyl] -6-〇-methyl- 2-[(Z)-11- (Octadecenylamino)] -4,10-Leptanoic acid group, β-D-D than glucosyl group} -2,3-dioxoyl-12-yl-β-D-glucopyranose Sugar methanesulfonic acid, 2-mono (quanyloxy) ethyl 6-〇- {2-deoxy-3—〇-[(R) — 3-methoxydecyl] _2— [(Z) — 11 — (Octadecenylamino)] — 4 101 Acid-β-D-glucopyranosyl} -2,3-1210-dodecyl-a-D-glucopyranoside, 2- (phosphonooxy) ethyl 6-0- { 2-deoxy-3-0-[(R) -3-hydroxydecyl] -2-[(Z) -11- (octadecenylamino)]-4--0-scale acid-β — D —pyranoglucosyl} —2 ′ 3 —dioxalyl-12 exyl —ex — D —glucopyranoside, 2- (phosphonooxy) ethyl 6 —〇— {2—go Oxy 3-O-[[R] -3-methoxydecyl] -6-O-methyl-2-[(Z) — Η- (octadecenylamino)]-4 -〇-1 Phosphonate-β-D-glucopyranosyl- 3-0-dodecyl-2-0-[(3-oxy) tetradecyl] -a-D-glucopyranoside, 2- (Phosphonic acidoxy) ethyl 6—〇— {2 —deoxy—3 — ◦-[(R) — 3-methoxydecyl] — 6 —〇—methyl—2 — [(Z) — Η One (eighteen carbon storage amine group)] one 4 one 10-phosphonic acid group-β-D-glucopyranosyl group-one 2,3-bis one-one [(nonyloxy) ethyl] one α- D -234-200413400 -glucopyranose , 2- (phosphonooxy) ethyl 6-0- {2-deoxy-3-0-[(R) -3-methoxydecyl] -6-0-methyl-1 2-[(Z ) — 11 — (octadecenylamino)] 4-◦ monophosphonic acid group β-D-glucopyranosyl group-2, 3-bis-10-{2-[2-( (Oxy) ethoxy] ethyl} —α-D-glucopyranoside, 2- (phosphonooxy) ethyl 6—〇— {2 —deoxy—3—〇 — [(R) — 3 —Methoxydecyl] -6—〇-methyl-2 — [(Z) — 11— (octadecenylamino)] — 4—monophosphonic acid—β-D-glucopyranose } —2,3—bis-101—2— [2— (2-propoxyethoxy) ethoxy] ethyl} —a—D—glucopyranoside, 2- (phosphonic acid oxygen Ethyl) ethyl 6 — ◦ — {2 —deoxy-3—〇 — [(R) — 3-methoxydecyl] —6 —〇-methyl-2 — [(Z) — 11 — (eighteen Carbaminamido)] -4 10-phosphonic acid group-β-D-glucopyranosyl group-3-10-11 · group-2-0-[2-(~ ) Ethyl] -a-D-glucopyranoside, 2- (phosphine) Oxy) ethyl 6 —〇— {2 —deoxy—3—〇 — [(R) — 3 —methoxydecyl] — 6 —〇—methyl—2 — [(Z) — 11 — (ten Octacarbenylamino)]-4 monophosphonic acid group β-D-glucopyranosyl group} -2,3-bis-10 [[(non-pentyl) ethyl] -α — D —glucopyranoside, 2- (phosphonooxy) ethyl 6—〇— {2 —deoxy—3—〇 — [(R) — 3 —methoxydecyl] —6—〇-methyl 2-([Z) —11— (octadecenylamino)] — 4-—monophosphonic acid—β—D—pyridine-235—200413400—Glucosyl 丨 —3— Diyl-2-O _ [(3-oxy) tetradecanyl)] α-D-glucopyranoside, phosphonate 6-0- {2-deoxy-3-0-[[R ) —3-Methoxydecyl] -6-〇-methyl-1 2-[(Z) — 11- (octadecylaminoamido)]-4-10-phosphonic acid group β-D-pyran Glucosyl 丨 3 10 12 yl 2-0-[(3-oxy) tetradecyl fluorenyl]-α-D-glucopyranoside or phosphonic acid 6-0-{2 — Deoxygenated 3 — Mono [(R) —3-methoxydecyl] — 6 —〇-methyl — 2 — [(Z) — 11 ((octadecenylamino)] — 4 — 0 — phosphonic acid — β —D ~ 〇 Gluconosyl} -3-O-12-dodecyl-2-0-[(3-oxy) tetradecanylamido] -β-D-glucopyranoside. 48-A medicinal composition containing the compound according to any one of claims 1 to 46 or a pharmacologically acceptable salt thereof as an active ingredient. 4 9 · An inflammation preventive or therapeutic agent containing the compound according to any one of claims 1 to 46 or the pharmacologically acceptable salt thereof as an active ingredient. 50 ·-a preventive agent for autoimmune diseases or The therapeutic agent contains the compound according to any one of claims 1 to 46 or a pharmacologically acceptable salt thereof as an active ingredient. 5 1 · — A preventive or therapeutic agent for septicemia, which contains the compound according to any one of claims 1 to 46 or its pharmacologically acceptable salt as an effective ingredient. 5 2 · An immunosuppressant containing the compound of any one of 200413400 or the pharmacologically acceptable salt thereof as the active ingredient in the scope of patent applications No. 1 to 46. 5 3 kinds of prognostic improvement agents after coronary artery bypass formation, containing the compound of any one of items 1 to 4 of δ 円 Patent Range ϋΐ, or its pharmacological capacity, the noon salt is the active ingredient 54 • A use It is used to manufacture a pharmaceutical composition using the compound or any of its pharmacologically acceptable salts as described in any of claims 1 to 46 in the scope of patent application. 5 5 • A method for preventing or treating a disease is to administer a pharmacologically effective amount of a compound according to any one of the patent scope 1 to 46 or a pharmacologically acceptable salt thereof to a warm-blooded animal.

-237-200413400 柒 Designated representative map: (1) The designated representative map in this case is: None. (2) Brief description of the representative symbols of the components in this representative drawing: 捌 If there is a chemical formula in this case, please disclose the chemical formula that can best show the characteristics of the invention