JPS60163892A - 光学活性な重水素化糖の製造法 - Google Patents

光学活性な重水素化糖の製造法

Info

Publication number: JPS60163892A
Authority: JP; Japan
Prior art keywords: anhydro; group; formula; derivative; general formula
Prior art date: 1984-02-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP59016971A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0533234B2 (da

Inventor

Hiromu Meguro

目黒　煕

Hiroshi Orui

洋大類

Hisashi Kishi

久岸

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Meiji Seika Kaisha Ltd

Original Assignee

Meiji Seika Kaisha Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-02-03

Filing date

1984-02-03

Publication date

1985-08-26

1984-02-03 Application filed by Meiji Seika Kaisha Ltd filed Critical Meiji Seika Kaisha Ltd

1984-02-03 Priority to JP59016971A priority Critical patent/JPS60163892A/ja

1985-08-26 Publication of JPS60163892A publication Critical patent/JPS60163892A/ja

1993-05-19 Publication of JPH0533234B2 publication Critical patent/JPH0533234B2/ja

Status Granted legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title abstract description 6
150000001720 carbohydrates Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 31
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 13
229910052805 deuterium Inorganic materials 0.000 claims abstract description 13
125000006239 protecting group Chemical group 0.000 claims abstract description 11
125000002252 acyl group Chemical group 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
230000000707 stereoselective effect Effects 0.000 claims abstract description 5
238000007142 ring opening reaction Methods 0.000 claims abstract description 4
230000002829 reductive effect Effects 0.000 claims description 31
238000004519 manufacturing process Methods 0.000 claims description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 20
229960003082 galactose Drugs 0.000 claims description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
239000003513 alkali Substances 0.000 claims description 11
235000014113 dietary fatty acids Nutrition 0.000 claims description 10
229930195729 fatty acid Natural products 0.000 claims description 10
239000000194 fatty acid Substances 0.000 claims description 10
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
-1 benzylsulfonyl Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Chemical group 0.000 claims description 7
150000004665 fatty acids Chemical class 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001118 alkylidene group Chemical group 0.000 claims description 4
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 4
FAOSYNUKPVJLNZ-UHFFFAOYSA-N butylstannane Chemical compound CCCC[SnH3] FAOSYNUKPVJLNZ-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 3
230000020176 deacylation Effects 0.000 claims description 3
238000005947 deacylation reaction Methods 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
238000007256 debromination reaction Methods 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
239000011592 zinc chloride Substances 0.000 claims description 2
235000005074 zinc chloride Nutrition 0.000 claims description 2
239000012528 membrane Substances 0.000 claims 3
TWNIBLMWSKIRAT-FPRJBGLDSA-N (1r,2r,3s,4r,5r)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol Chemical class O1[C@@]2([H])OC[C@]1([H])[C@H](O)[C@H](O)[C@H]2O TWNIBLMWSKIRAT-FPRJBGLDSA-N 0.000 claims 1
OYJJPEGOLXZHDM-TXICZTDVSA-N (1r,2s,3r,4r)-5,7-dioxabicyclo[2.2.1]heptane-2,3-diol Chemical class O1C[C@@H]2[C@@H](O)[C@@H](O)[C@H]1O2 OYJJPEGOLXZHDM-TXICZTDVSA-N 0.000 claims 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
239000008101 lactose Substances 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 abstract description 5
238000005695 dehalogenation reaction Methods 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
238000005658 halogenation reaction Methods 0.000 abstract 1
238000002372 labelling Methods 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000377 silicon dioxide Substances 0.000 description 18
239000013078 crystal Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
235000000346 sugar Nutrition 0.000 description 12
239000002904 solvent Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
238000001816 cooling Methods 0.000 description 10
238000010992 reflux Methods 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 7
235000012239 silicon dioxide Nutrition 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 5
229930182830 galactose Natural products 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 4
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000003756 stirring Methods 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical class CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000003999 initiator Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
239000004299 sodium benzoate Substances 0.000 description 2
235000010234 sodium benzoate Nutrition 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
125000002130 sulfonic acid ester group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WQZGKKKJIJFFOK-DHVFOXMCSA-N L-galactose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-DHVFOXMCSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
JTFITTQBRJDSTL-KVTDHHQDSA-N S-methyl-5-thio-alpha-D-ribose 1-phosphate Chemical compound CSC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H]1O JTFITTQBRJDSTL-KVTDHHQDSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
235000002597 Solanum melongena Nutrition 0.000 description 1
208000033809 Suppuration Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
PMIIFNFHVJSOAN-UHFFFAOYSA-N acetic acid;thorium Chemical compound [Th].CC(O)=O PMIIFNFHVJSOAN-UHFFFAOYSA-N 0.000 description 1
PYMYPHUHKUWMLA-MROZADKFSA-N aldehydo-L-ribose Chemical compound OC[C@H](O)[C@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-MROZADKFSA-N 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000004767 nitrides Chemical class 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003290 ribose derivatives Chemical class 0.000 description 1
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ZIPSUOPRDBUYPW-UHFFFAOYSA-J thorium(4+) tetrabenzoate Chemical compound C(C1=CC=CC=C1)(=O)[O-].[Th+4].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-] ZIPSUOPRDBUYPW-UHFFFAOYSA-J 0.000 description 1
DBGVGMSCBYYSLD-RCUQKECRSA-N tributyl(deuterio)stannane Chemical compound CCCC[Sn]([2H])(CCCC)CCCC DBGVGMSCBYYSLD-RCUQKECRSA-N 0.000 description 1
ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Investigating Or Analysing Biological Materials (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP59016971A 1984-02-03 1984-02-03 光学活性な重水素化糖の製造法 Granted JPS60163892A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP59016971A JPS60163892A (ja)	1984-02-03	1984-02-03	光学活性な重水素化糖の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59016971A JPS60163892A (ja)	1984-02-03	1984-02-03	光学活性な重水素化糖の製造法

Publications (2)

Publication Number	Publication Date
JPS60163892A true JPS60163892A (ja)	1985-08-26
JPH0533234B2 JPH0533234B2 (da)	1993-05-19

Family

ID=11930962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59016971A Granted JPS60163892A (ja)	1984-02-03	1984-02-03	光学活性な重水素化糖の製造法

Country Status (1)

Country	Link
JP (1)	JPS60163892A (da)

1984
- 1984-02-03 JP JP59016971A patent/JPS60163892A/ja active Granted

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CANADION J OF CHEMISTRY=1971 *
CARBOHYDRATE RESEARCH=1977 *

Also Published As

Publication number	Publication date
JPH0533234B2 (da)	1993-05-19

Publication	Publication Date	Title
WO1990015812A1 (en)	1990-12-27	Intermediate for 2-alkynyladenosine synthesis, production of said intermediate, production of 2-alkynyladenosine from said intermediate, and stable 2-alkynyladenosine derivative
JPS61204193A (ja)	1986-09-10	シトシンヌクレオシド類の製造法
JPS6345293A (ja)	1988-02-26	シアロシルセラミド類及びその製造方法
US5633366A (en)	1997-05-27	Pyrimidine nucleoside derivatives and methods for producing them
Su et al.	1982	Improved synthesis of. alpha.-D-ribofuranosides via stereoselective alkylation of a dibutylstannylene derivative for ready access to the 2-substituted 2-deoxyarabinofuranosides
Su et al.	1981	Facile synthesis of 2-deoxy-2-substituted D-arabinofuranose derivatives
Streicher et al.	2003	Synthesis of amino-substituted hexo-and heptopyranoses from d-galactose
Spak et al.	2000	The Synthesis of an O, C-Trisaccharide: The O, C-Analog of Methyl 4′-O-β-d-glucopyranosylgentiobioside
JPS60163892A (ja)	1985-08-26	光学活性な重水素化糖の製造法
Joe et al.	2006	Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates
Jürs et al.	2005	Alternative approaches towards glycosylated eight-membered ring compounds employing Claisen rearrangement of mono and disaccharide allyl vinyl ether precursors
EP1829884B1 (en)	2010-11-10	Sugar donor
Witczak et al.	2002	Thiosugars VI: A Simple Stereoselective Approach to (1→ 3)-3-S-Thiodisaccharides from Levoglucosenone
Carmona et al.	1999	Branched-chain fluoro nitro d-and l-sugars from glucose
US4496485A (en)	1985-01-29	Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones
Nagy et al.	2009	Synthesis of some O-, S-and N-glycosides of hept-2-ulopyranosonamides
Maity et al.	2007	First example of 5/6-O-linked pseudosaccharides: synthesis of bicyclic nucleosides containing azido or extended carbohydrate moiety
Allen et al.	2010	Syntheses of novel azasugar-containing mimics of heparan sulfate fragments as potential heparanase inhibitors
PL187648B1 (pl)	2004-08-31	Sposób wytwarzania pochodnej deoksyurydyny
Bodenteich et al.	1993	Synthesis of carbocyclic analogs of 1-. beta.-D-psicofuranosyl nucleosides. psico-Cyclopentenyladenosine (psicoplanocin A) and psico-cyclopentenylcytosine
Gómez et al.	2005	Synthesis of 2, 3: 4, 6-di-O-isopropylidene-D-allopyranose from D-glucose
JP3053863B2 (ja)	2000-06-19	２―アルキニルアデノシンの合成中間体、該合成中間体の製造法、該合成中間体を利用した２―アルキニルアデノシンの製造法および安定な２―アルキニルアデノシン誘導体
Mastihubová et al.	2004	An efficient chemoenzymatic route to methyl 4-O-benzyl-2, 3-anhydro-β-d-lyxopyranoside from methyl β-d-xylopyranoside
JP4169583B2 (ja)	2008-10-22	光学活性デオキシイノシトールリン酸エステル誘導体及びそれらの製造法
Mackle	2022	Synthetic Efforts Towards the Total Synthesis of the Nucleoside Antibiotic,(+)-Amicetin