CN1587273A - 20(S)-人参皂苷Rh2的合成方法 - Google Patents
20(S)-人参皂苷Rh2的合成方法 Download PDFInfo
- Publication number
- CN1587273A CN1587273A CNA2004100532692A CN200410053269A CN1587273A CN 1587273 A CN1587273 A CN 1587273A CN A2004100532692 A CNA2004100532692 A CN A2004100532692A CN 200410053269 A CN200410053269 A CN 200410053269A CN 1587273 A CN1587273 A CN 1587273A
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- China
- Prior art keywords
- reaction
- compound
- protopanoxadiol
- synthetic method
- ginsenoside
- Prior art date
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- CKUVNOCSBYYHIS-IRFFNABBSA-N (20S)-ginsenoside Rh2 Chemical compound O([C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4[C@@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CKUVNOCSBYYHIS-IRFFNABBSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title abstract description 28
- CKUVNOCSBYYHIS-UHFFFAOYSA-N (20R)-ginsenoside Rg3 Natural products CC(C)=CCCC(C)(O)C1CCC(C2(CCC3C4(C)C)C)(C)C1C(O)CC2C3(C)CCC4OC1OC(CO)C(O)C(O)C1O CKUVNOCSBYYHIS-UHFFFAOYSA-N 0.000 title abstract description 18
- 230000002194 synthesizing effect Effects 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 84
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 9
- 238000000746 purification Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 238000010189 synthetic method Methods 0.000 claims description 22
- 238000006206 glycosylation reaction Methods 0.000 claims description 21
- 238000001953 recrystallisation Methods 0.000 claims description 21
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 14
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
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- 125000002252 acyl group Chemical group 0.000 claims description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
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- 239000003795 chemical substances by application Substances 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 6
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- CKUVNOCSBYYHIS-LGYUXIIVSA-N 20(R)-Ginsenoside Rh2 Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1C(C)(C)[C@H]2[C@@](C)([C@H]3[C@](C)([C@@]4(C)[C@H]([C@H](O)C3)[C@@H]([C@](O)(CC/C=C(\C)/C)C)CC4)CC2)CC1 CKUVNOCSBYYHIS-LGYUXIIVSA-N 0.000 description 8
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 7
- 229940089161 ginsenoside Drugs 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
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- 229910001958 silver carbonate Inorganic materials 0.000 description 4
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- RWXIFXNRCLMQCD-JBVRGBGGSA-N (20S)-ginsenoside Rg3 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4[C@@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RWXIFXNRCLMQCD-JBVRGBGGSA-N 0.000 description 2
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- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (11)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100532692A CN1252083C (zh) | 2004-07-29 | 2004-07-29 | 20(S)-人参皂苷Rh2的合成方法 |
KR1020067015972A KR100913010B1 (ko) | 2004-07-29 | 2005-05-16 | 20〔S〕-진세노사이드 Rh2의 합성 방법 |
JP2007522899A JP4856071B2 (ja) | 2004-07-29 | 2005-05-16 | 20(S)−ジンセノサイドRh2の合成方法 |
PCT/CN2005/000675 WO2006010307A1 (fr) | 2004-07-29 | 2005-05-16 | Synthese du 20 (s)-ginsenoside rh2 |
US11/630,751 US20080275225A1 (en) | 2004-07-29 | 2005-05-16 | Synthetic Method of 20 (S)-Ginsenoside Rh2 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100532692A CN1252083C (zh) | 2004-07-29 | 2004-07-29 | 20(S)-人参皂苷Rh2的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1587273A true CN1587273A (zh) | 2005-03-02 |
CN1252083C CN1252083C (zh) | 2006-04-19 |
Family
ID=34602800
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004100532692A Expired - Fee Related CN1252083C (zh) | 2004-07-29 | 2004-07-29 | 20(S)-人参皂苷Rh2的合成方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20080275225A1 (zh) |
JP (1) | JP4856071B2 (zh) |
KR (1) | KR100913010B1 (zh) |
CN (1) | CN1252083C (zh) |
WO (1) | WO2006010307A1 (zh) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1651451B (zh) * | 2004-12-10 | 2011-06-08 | 海南亚洲制药有限公司 | 20(s)-原人参二醇衍生物、含有它们的药物组合物及其应用 |
CN102336800A (zh) * | 2011-07-22 | 2012-02-01 | 中国科学院上海有机化学研究所 | 一种20位接糖的原人参三醇类人参皂苷及类似物的合成方法 |
CN102731604A (zh) * | 2011-03-31 | 2012-10-17 | 上海兰蒂斯生物医药科技有限公司 | 20(R)-人参皂苷Rh2的合成方法 |
WO2014086317A1 (zh) | 2012-12-06 | 2014-06-12 | 中国科学院上海生命科学研究院 | 一组糖基转移酶及其应用 |
CN104447895A (zh) * | 2014-10-24 | 2015-03-25 | 济南卡博唐生物科技有限公司 | 一种五特戊酰基吡喃葡萄糖的制备方法 |
CN105461767A (zh) * | 2014-08-07 | 2016-04-06 | 富力 | 一种连翘苷的化学合成方法 |
CN105801661A (zh) * | 2016-04-29 | 2016-07-27 | 吉林省君诚生物科技开发有限公司 | 一种人参皂苷新衍生物的合成方法和生产的产品及其应用 |
CN113480591A (zh) * | 2021-05-27 | 2021-10-08 | 吉林大学 | 一种人参皂苷衍生物及其合成方法与应用 |
Families Citing this family (4)
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---|---|---|---|---|
KR101098027B1 (ko) | 2009-09-18 | 2011-12-27 | 한국과학기술원 | 로다노박터 진세노시디뮤탄스 kctc22231t 유래의 진세노시드 글리코시다제 및 이의 용도 |
CN103360442B (zh) * | 2012-03-30 | 2016-03-30 | 中国科学院上海有机化学研究所 | 一种原人参三醇类人参皂苷的制备方法 |
JP6201823B2 (ja) * | 2014-03-05 | 2017-09-27 | 株式会社ツムラ | 4’−o−グルコシル−5−o−メチルビサミノールの製造方法 |
CN114702540A (zh) * | 2022-01-23 | 2022-07-05 | 吉林农业大学 | 化合物20(s)-原人参二醇ppd的制备新方法与应用 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR940004066B1 (ko) * | 1991-09-20 | 1994-05-11 | 재단법인 한국인삼연초연구소 | 인삼 성분으로부터 20(r & s) 진세노사이드를 제조하는 방법 |
KR940008291B1 (ko) * | 1991-09-20 | 1994-09-10 | 재단법인 한국인삼연초연구소 | 신물질 20(R)-전세노사이드 Rh₂ |
KR950007250B1 (ko) * | 1992-04-15 | 1995-07-07 | 주식회사대웅제약 | 사포닌의 제조방법 |
KR960003662B1 (ko) * | 1993-08-25 | 1996-03-21 | 대우전자주식회사 | 220v용 브이 씨 알의 110v 입력시 동작 방지 회로 |
JP3535588B2 (ja) * | 1994-11-18 | 2004-06-07 | 株式会社ネオス | ジンセノサイドRh2の製造方法 |
KR0148717B1 (ko) * | 1995-08-30 | 1998-08-01 | 박명규 | 진세노사이드 유도체 및 그것의 제조방법 |
AU6121898A (en) * | 1997-03-12 | 1998-09-29 | Taisho Pharmaceutical Co., Ltd. | Sterol compounds |
CN1091448C (zh) * | 1998-02-05 | 2002-09-25 | 沈阳天马医药科技开发有限公司 | 20(S)-人参皂甙-Rh2的制备 |
KR100293968B1 (ko) * | 1998-12-30 | 2001-09-17 | 박명규 | 20(에스)-진세노사이드알에이취투의제조방법 |
US6753414B2 (en) * | 2001-08-07 | 2004-06-22 | University Of Iowa Research Foundation, Inc. | Process for preparing saponin compounds |
-
2004
- 2004-07-29 CN CNB2004100532692A patent/CN1252083C/zh not_active Expired - Fee Related
-
2005
- 2005-05-16 KR KR1020067015972A patent/KR100913010B1/ko active IP Right Grant
- 2005-05-16 WO PCT/CN2005/000675 patent/WO2006010307A1/zh active Application Filing
- 2005-05-16 US US11/630,751 patent/US20080275225A1/en not_active Abandoned
- 2005-05-16 JP JP2007522899A patent/JP4856071B2/ja not_active Expired - Fee Related
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1651451B (zh) * | 2004-12-10 | 2011-06-08 | 海南亚洲制药有限公司 | 20(s)-原人参二醇衍生物、含有它们的药物组合物及其应用 |
CN102731604A (zh) * | 2011-03-31 | 2012-10-17 | 上海兰蒂斯生物医药科技有限公司 | 20(R)-人参皂苷Rh2的合成方法 |
CN102336800A (zh) * | 2011-07-22 | 2012-02-01 | 中国科学院上海有机化学研究所 | 一种20位接糖的原人参三醇类人参皂苷及类似物的合成方法 |
CN102336800B (zh) * | 2011-07-22 | 2014-03-05 | 中国科学院上海有机化学研究所 | 一种20位接糖的原人参三醇类人参皂苷及类似物的合成方法 |
CN107058446A (zh) * | 2012-12-06 | 2017-08-18 | 中国科学院上海生命科学研究院 | 一组糖基转移酶及其应用 |
WO2014086317A1 (zh) | 2012-12-06 | 2014-06-12 | 中国科学院上海生命科学研究院 | 一组糖基转移酶及其应用 |
US9976167B2 (en) | 2012-12-06 | 2018-05-22 | Shanghai Institutes For Biological Sciences, Chinese Academy Of Sciences | Group of glycosyltransferases and use thereof |
CN107058446B (zh) * | 2012-12-06 | 2021-10-22 | 中国科学院分子植物科学卓越创新中心 | 一组糖基转移酶及其应用 |
EP3985110A1 (en) | 2012-12-06 | 2022-04-20 | CAS Center for Excellence in Molecular Plant Sciences | Group of glycosyltransferases and use thereof |
EP4043560A2 (en) | 2012-12-06 | 2022-08-17 | CAS Center for Excellence in Molecular Plant Sciences | Group of glycosyltransferases and use thereof |
CN105461767A (zh) * | 2014-08-07 | 2016-04-06 | 富力 | 一种连翘苷的化学合成方法 |
CN105461767B (zh) * | 2014-08-07 | 2019-03-12 | 富力 | 一种连翘苷的化学合成方法 |
KR102057549B1 (ko) * | 2014-08-07 | 2019-12-19 | 리 푸 | 필리린에 대한 화학적 합성 방법 |
CN104447895A (zh) * | 2014-10-24 | 2015-03-25 | 济南卡博唐生物科技有限公司 | 一种五特戊酰基吡喃葡萄糖的制备方法 |
CN105801661A (zh) * | 2016-04-29 | 2016-07-27 | 吉林省君诚生物科技开发有限公司 | 一种人参皂苷新衍生物的合成方法和生产的产品及其应用 |
CN113480591A (zh) * | 2021-05-27 | 2021-10-08 | 吉林大学 | 一种人参皂苷衍生物及其合成方法与应用 |
Also Published As
Publication number | Publication date |
---|---|
JP2008508194A (ja) | 2008-03-21 |
US20080275225A1 (en) | 2008-11-06 |
CN1252083C (zh) | 2006-04-19 |
WO2006010307A1 (fr) | 2006-02-02 |
JP4856071B2 (ja) | 2012-01-18 |
KR100913010B1 (ko) | 2009-08-20 |
KR20070040327A (ko) | 2007-04-16 |
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