JPS58208286A - ビスビベンジルジエ−テル誘導体 - Google Patents

ビスビベンジルジエ−テル誘導体

Info

Publication number: JPS58208286A
Authority: JP; Japan
Prior art keywords: compound; group; ethyl acetate; formula; reaction
Prior art date: 1982-05-28
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

JP57091883A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0239506B2 (da

Inventor

Yoshinori Asakawa

義範浅川

Tsunematsu Takemoto

竹本　常松

Masao Toyoda

豊田　正夫

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.)

Otsuka Pharmaceutical Co Ltd

Original Assignee

Otsuka Pharmaceutical Co 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.)

1982-05-28

Filing date

1982-05-28

Publication date

1983-12-03

1982-05-28 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1982-05-28 Priority to JP57091883A priority Critical patent/JPS58208286A/ja

1983-12-03 Publication of JPS58208286A publication Critical patent/JPS58208286A/ja

1990-09-05 Publication of JPH0239506B2 publication Critical patent/JPH0239506B2/ja

Status Granted legal-status Critical Current

Links

150000002170 ethers Chemical class 0.000 title description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
125000002252 acyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 29
239000003795 chemical substances by application Substances 0.000 abstract description 10
-1 methylenedioxy Chemical group 0.000 abstract description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
238000000926 separation method Methods 0.000 abstract description 4
238000004440 column chromatography Methods 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
238000000605 extraction Methods 0.000 abstract description 2
125000004423 acyloxy group Chemical group 0.000 abstract 2
230000003327 cancerostatic effect Effects 0.000 abstract 2
241000196329 Marchantia polymorpha Species 0.000 abstract 1
LLMFFOXSSQHNFR-UHFFFAOYSA-N Marchantin A Chemical compound O1C2=C(O)C=CC=C2CCC(C=C2)=CC=C2OC(C=2)=C(O)C(O)=CC=2CCC2=CC=CC1=C2 LLMFFOXSSQHNFR-UHFFFAOYSA-N 0.000 abstract 1
241001503397 Reboulia Species 0.000 abstract 1
241001003158 Riccardia multifida Species 0.000 abstract 1
SCWKUSONPRYOHV-UHFFFAOYSA-N marchantin A Natural products Oc1cccc2CCc3ccc(Oc4cc(CCc5ccccc5Oc12)cc(O)c4O)cc3 SCWKUSONPRYOHV-UHFFFAOYSA-N 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
238000002360 preparation method Methods 0.000 abstract 1
230000001988 toxicity Effects 0.000 abstract 1
231100000419 toxicity Toxicity 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000004519 manufacturing process Methods 0.000 description 16
238000010828 elution Methods 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
230000000704 physical effect Effects 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000011521 glass Substances 0.000 description 10
238000000034 method Methods 0.000 description 10
238000005917 acylation reaction Methods 0.000 description 9
239000000499 gel Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
150000007514 bases Chemical class 0.000 description 5
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000003814 drug Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000401 methanolic extract Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000007976 Ketosis Diseases 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000004020 conductor Substances 0.000 description 2
229960004643 cupric oxide Drugs 0.000 description 2
238000001647 drug administration Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
230000004140 ketosis Effects 0.000 description 2
238000011068 loading method Methods 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 2
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
PCFGFYKGPMQDBX-FEKONODYSA-N 78355-50-7 Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 PCFGFYKGPMQDBX-FEKONODYSA-N 0.000 description 1
235000016626 Agrimonia eupatoria Nutrition 0.000 description 1
241000357297 Atypichthys strigatus Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101150040772 CALY gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000006145 Eagle's minimal essential medium Substances 0.000 description 1
NVGBPTNZLWRQSY-UWVGGRQHSA-N Lys-Lys Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CCCCN NVGBPTNZLWRQSY-UWVGGRQHSA-N 0.000 description 1
241000196322 Marchantia Species 0.000 description 1
241000196323 Marchantiophyta Species 0.000 description 1
NEAPKZHDYMQZCB-UHFFFAOYSA-N N-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]ethyl]-2-oxo-3H-1,3-benzoxazole-6-carboxamide Chemical compound C1CN(CCN1CCNC(=O)C2=CC3=C(C=C2)NC(=O)O3)C4=CN=C(N=C4)NC5CC6=CC=CC=C6C5 NEAPKZHDYMQZCB-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 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
230000001093 anti-cancer Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
108010054155 lysyllysine Proteins 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
108010069653 peptide E (adrenal medulla) Proteins 0.000 description 1
108010091742 peptide F Proteins 0.000 description 1
RJSZPKZQGIKVAU-UXBJKDEOSA-N peptide f Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C(C)C)C(C)C)C1=CC=CC=C1 RJSZPKZQGIKVAU-UXBJKDEOSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
239000000243 solution Substances 0.000 description 1
RUJLHPZAKCVICY-UHFFFAOYSA-J thorium(4+);disulfate Chemical compound [Th+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUJLHPZAKCVICY-UHFFFAOYSA-J 0.000 description 1
230000014616 translation Effects 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Pyrane Compounds (AREA)

JP57091883A 1982-05-28 1982-05-28 ビスビベンジルジエ−テル誘導体 Granted JPS58208286A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP57091883A JPS58208286A (ja)	1982-05-28	1982-05-28	ビスビベンジルジエ−テル誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57091883A JPS58208286A (ja)	1982-05-28	1982-05-28	ビスビベンジルジエ−テル誘導体

Publications (2)

Publication Number	Publication Date
JPS58208286A true JPS58208286A (ja)	1983-12-03
JPH0239506B2 JPH0239506B2 (da)	1990-09-05

Family

ID=14038955

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57091883A Granted JPS58208286A (ja)	1982-05-28	1982-05-28	ビスビベンジルジエ−テル誘導体

Country Status (1)

Country	Link
JP (1)	JPS58208286A (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005092323A1 (ja) *	2004-03-29	2005-10-06	Japan Health Sciences Foundation	LXRα受容体特異的部分アゴニスト
CN113549046A (zh) *	2021-06-23	2021-10-26	山东大学	一种双联苄地钱素s衍生物及其制备方法和应用

1982
- 1982-05-28 JP JP57091883A patent/JPS58208286A/ja active Granted

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005092323A1 (ja) *	2004-03-29	2005-10-06	Japan Health Sciences Foundation	LXRα受容体特異的部分アゴニスト
JPWO2005092323A1 (ja) *	2004-03-29	2008-02-07	財団法人ヒューマンサイエンス振興財団	ＬＸＲα受容体特異的部分アゴニスト
JP5028594B2 (ja) *	2004-03-29	2012-09-19	財団法人ヒューマンサイエンス振興財団	ＬＸＲα受容体特異的部分アゴニスト
CN113549046A (zh) *	2021-06-23	2021-10-26	山东大学	一种双联苄地钱素s衍生物及其制备方法和应用

Also Published As

Publication number	Publication date
JPH0239506B2 (da)	1990-09-05

Publication	Publication Date	Title
EP0526642A1 (en)	1993-02-10	Triterpene derivative
Cupps et al.	1982	Use of allyltrimethylsilane in the formation of potential C-nucleoside precursors
US3862121A (en)	1975-01-21	Ether and ester substituted d-glycofuranoside compounds
Flowers	1975	Selective benzylation of some D-galactopyranosides. Unusual relative reactivity of the hydroxyl group at C-4
Stoessl	1969	Relative stereochemistry of altersolanol A
CN106749446A (zh)	2017-05-31	一种盐酸表柔比星中间体化合物ⅴ
SU634674A3 (ru)	1978-11-25	Способ получени оптически активных производных эбурнаменина или их солей
US3781267A (en)	1973-12-25	O-esters of monosaccharides having ether groupings
JPS58208286A (ja)	1983-12-03	ビスビベンジルジエ−テル誘導体
Chittenden	1970	Oxidation of some derivatives of d-galactose with methyl sulphoxide-acid anhydride mixtures: a route to derivatives of d-glucose and d-talose
Han et al.	1993	Investigations of the formation of cyclic acetal and ketal derivatives of D-ribono-1, 4-lactone and 2-deoxy-D-ribono-1, 4-lactone
Demuth et al.	1989	Iridoid glucosides from Asystasia bella
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KUBO et al.	1980	Studies on the Constituents of Aceraceae Plants. III. Strucure of Acerogenin B from Acer nikoense MAXIM.
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Katsui et al.	1982	Structure of epilubimin, epioxylubimin, and isolubimin, spirovetivane stress metabolites in diseased potato.
Johansson et al.	1966	Deoxyfluoro sugars: Part I. Synthesis of 2-deoxy-2-fluoro-D-altrose, 2-deoxy-2-fluoro-D-allose, and 3-deoxy-3-fluoro-D-glucose
Wood Jr et al.	1958	The Preparation of Crystalline 2-O-Methylsulfonyl-D-arabinose and Some of Its Derivatives
CA2768948A1 (en)	2011-02-03	Process for producing thiabenzoazulene-propionic acid derivative
Williams et al.	1969	Synthesis of D-glycero-D-gulo-heptose, D-glycero-D-ido-heptose, and 2-deoxy-D-gluco-heptose from D-glucose
Jordaan et al.	1968	The structure and synthesis of pavettine, an alkaloid from Pavetta lanceolata Eckl.(Rubiaceae)
Sinclair	1965	An improved method for the preparation of methyl 6-chloro-6-deoxy-α-D-glucopyranoside