RU2006127553A - Новые оптические активные, гетероароматические в-гидроксиэстеры, способы их получения из в-кетоэстеров, а также способы получения таких в-кетоэстеров - Google Patents
Новые оптические активные, гетероароматические в-гидроксиэстеры, способы их получения из в-кетоэстеров, а также способы получения таких в-кетоэстеров Download PDFInfo
- Publication number
- RU2006127553A RU2006127553A RU2006127553/04A RU2006127553A RU2006127553A RU 2006127553 A RU2006127553 A RU 2006127553A RU 2006127553/04 A RU2006127553/04 A RU 2006127553/04A RU 2006127553 A RU2006127553 A RU 2006127553A RU 2006127553 A RU2006127553 A RU 2006127553A
- Authority
- RU
- Russia
- Prior art keywords
- saccharomyces
- candida
- compound according
- general formula
- compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
- C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/14—Nitrogen or oxygen as hetero atom and at least one other diverse hetero ring atom in the same ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (24)
1. Соединение общей формулы I, представленное двумя изомерами
где А представляет собой бициклический гетероароматический остаток формулы
где «гетероароматический» означает 5- или 6-членное гетероароматическое кольцо, содержащее вплоть до 2 гетероатомов, выбранных из кислорода, азота или серы, которое является необязательно замещенным одним или двумя заместителями, выбранными из алкила, необязательного защищенного гидроксиалкила, галоалкила, галогена или CN; a R означает неразветвленную или разветвленную, необязательно насыщенную алкильную цепь, которая необязательно содержит 1-3 атома кислорода; фенил; циклогексил или бензил.
2. Соединение по п.1, в котором R представляет собой метил или этил.
8. Способ по п.7, в котором химическое восстановление осуществляют с помощью ассиметричного восстановления с использованием хирального металлического катализатора.
9. Способ по п.7, в котором микробиологическое восстановление осуществляют с помощью ассиметричного восстановления с использованием микроорганизмов видов baker's yeast, Brettanomyces bruxellensis, Candida albicans, Candida boidinii, Candida gropengiesseri, Candida guilliermondii, Candida kefyr, Candida pini, Candida rugosa, Candida solani, Candida tropicalis, Candida utilis, Candida valida, Clostridium beijerinckii, Clostridium pasteurianum, Cryptococcus laurentii, Cryptococcus macerans, Debaryomyces hansenii, Debaryomyces kloeckeri, Debaryomyces nicotianae, Debaryomyces vini, Endomycopsis fibuliger, Hanseniaspora guilliermondii, Hanseniaspora osmophila, Hanseniaspora uvarum, Hansenula capsulata, Hansenula holstii, Hansenula polymorpha, Hansenula saturnus, Hansenula silvicola, Issatchenkia orientalis, Kloeckera apiculata, Kloeckera corticis, Kloeckera javanica, Kloeckera sp., Kluyveromyces lactis, Kluyveromyces marxianus Kluveromyces sphaerica, Lactobacillus kefir, Nadsonia fulvescens, Octosporomyces octosporus, Pichia anomala, Pichia cactophila, Pichia farinosa, Pichia fermentans, Pichia holstii, Pichia jadinii, Pichia membranaefaciens, Pichia pijperi, Pichia silvicola, Pichia subpelliculosa, Pichia wickerhamii, Rhodotorula flava, Rhodotorula glutinis, Rhodotorula minuta var. minuta, Saccharomyces acidificans, Saccharomyces bailii, Saccharomyces bayanus, Saccharomyces carlsb. штамм Herrliberg, Saccharomyces carlsbergensis, Saccharomyces cerevisiae, Saccharomyces chevalieri, Saccharomyces exiguus, Saccharomycopsis fibuligera, Saccharomyces paradoxus, Saccharomyces pastorianus, Saccharomyces pastorianus ранее Saccharomycopsis capsularis, Saccharomyces sp., Schizosaccharomyces pombe, Schizosaccharomyces octosporus, Sporobolomyces coralliformis, Sporobolomyces salmonicolor, Torulopsis pinus, Trigonopsis varabilis, Tremella fuciformis, Waltomyces lipofer, Zygosaccharomyces fermentati или Zygosaccharomyces rouxii.
10. Способ по п.9, в котором используемый микроорганизм представляет собой Pichia wickerhamii (IFO 1278).
11. Применение соединения по пп.1-6, в качестве исходного или промежуточного продукта для общего синтеза производных эпотилона.
12. Применение способа по пп.7-10, для синтеза исходных или промежуточных продуктов для общего синтеза производных эпотилона.
14. Соединение по п.13, в котором R представляет собой метил или этил.
19. Способ получения β-кетоэстера общей формулы IV
как заявлено в любом из пп.13-18, из соединений общих формул VII и VIII,
в котором кислоту общей формулы VII сначала активируют с помощью N,N-карбодиимидазола, после чего осуществляют реакцию in situ с силиловым эстером, полученным путем депротонирования с помощью сильного основания соединения общей формулы VIII, и реакции с хлоридом триметилсилила, после чего осуществляют обработку водой.
20. Способ по п.19, в котором R представляет собой метил или этил.
21. Способ по п.19, в котором трет-бутилат калия используют в качестве сильного основания.
22. Способ по п.19, в котором прибавляют хлорид лития или бромид лития для лучшей перемешиваемости.
23. Применение соединения, как заявлено в любом из пп.13-18, в качестве исходных или промежуточных продуктов для общего синтеза производных эпотилона.
24. Применение способа по пп.19-22, для синтеза исходных или промежуточных продуктов для общего синтеза производных эпотилона.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10361794A DE10361794B3 (de) | 2003-12-31 | 2003-12-31 | Optisch aktive heteroaromatische ß-Hydroxy-Ester und Verfahren zu deren Herstellung sowie deren Verwendung als Zwischenprodukte bei der Epothilon-Totalsynthese |
DE10361794.9 | 2003-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
RU2006127553A true RU2006127553A (ru) | 2008-02-10 |
Family
ID=34716267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2006127553/04A RU2006127553A (ru) | 2003-12-31 | 2004-12-21 | Новые оптические активные, гетероароматические в-гидроксиэстеры, способы их получения из в-кетоэстеров, а также способы получения таких в-кетоэстеров |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP2113031A1 (ru) |
JP (1) | JP2007516999A (ru) |
KR (1) | KR20070029641A (ru) |
CN (1) | CN100510098C (ru) |
AU (1) | AU2004309076A1 (ru) |
BR (1) | BRPI0418254A (ru) |
CA (1) | CA2546981A1 (ru) |
CR (1) | CR8492A (ru) |
DE (1) | DE10361794B3 (ru) |
EC (1) | ECSP066740A (ru) |
HK (1) | HK1097000A1 (ru) |
IL (1) | IL175908A0 (ru) |
MX (1) | MXPA06007564A (ru) |
NO (1) | NO20063477L (ru) |
RU (1) | RU2006127553A (ru) |
WO (1) | WO2005064006A1 (ru) |
ZA (1) | ZA200606293B (ru) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104328152A (zh) * | 2014-10-13 | 2015-02-04 | 青岛科技大学 | 一种产朊酵母催化生产亚环己基烯醇的方法 |
CN108118004B (zh) * | 2017-12-15 | 2021-06-25 | 北京工商大学 | 一株喜仙人掌毕赤酵母在水果采后病害防治中的应用 |
CN110283733B (zh) * | 2019-06-20 | 2020-10-27 | 浙江工业大学 | 土星轮头酵母zjph1807及其应用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU7257096A (en) * | 1995-10-04 | 1997-04-28 | Fmc Corporation | Herbicidal 6-heterocyclic indazole derivatives |
US5942644A (en) * | 1997-05-27 | 1999-08-24 | Biocatalytics, Inc. | Precursors for the production of chiral vicinal aminoalcohols |
US6211412B1 (en) * | 1999-03-29 | 2001-04-03 | The University Of Kansas | Synthesis of epothilones |
PE20010116A1 (es) * | 1999-04-30 | 2001-02-15 | Schering Ag | Derivados de 6-alquenil-, 6-alquinil- y 6-epoxi-epotilona, procedimientos para su preparacion |
JP2001213874A (ja) * | 1999-07-22 | 2001-08-07 | Mercian Corp | イソクマリン誘導体の製造およびそのための中間体 |
DE10041470A1 (de) * | 2000-08-18 | 2002-02-28 | Schering Ag | 12,13-Cyclopropyl-Epothilon-Derivate, Verfahren zu deren Herstellung sowie ihre Verwendung in pharmazeutischen Präparaten |
WO2003029195A1 (fr) * | 2001-09-28 | 2003-04-10 | Sumika Fine Chemicals Co., Ltd. | Intermediaires pour l'elaboration d'un derive de l'epothilone, et leur procede de production |
JP4432315B2 (ja) * | 2002-03-19 | 2010-03-17 | 三菱化学株式会社 | 光学活性3−ヒドロキシ−3−(2’−チエニル)プロピオン酸エステル誘導体の製造方法 |
-
2003
- 2003-12-31 DE DE10361794A patent/DE10361794B3/de not_active Expired - Fee Related
-
2004
- 2004-12-21 RU RU2006127553/04A patent/RU2006127553A/ru not_active Application Discontinuation
- 2004-12-21 JP JP2006546092A patent/JP2007516999A/ja active Pending
- 2004-12-21 AU AU2004309076A patent/AU2004309076A1/en not_active Abandoned
- 2004-12-21 WO PCT/EP2004/014753 patent/WO2005064006A1/en active Application Filing
- 2004-12-21 KR KR1020067013057A patent/KR20070029641A/ko not_active Application Discontinuation
- 2004-12-21 EP EP04804342A patent/EP2113031A1/en not_active Withdrawn
- 2004-12-21 CA CA002546981A patent/CA2546981A1/en not_active Abandoned
- 2004-12-21 CN CNB2004800395725A patent/CN100510098C/zh not_active Expired - Fee Related
- 2004-12-21 MX MXPA06007564A patent/MXPA06007564A/es unknown
- 2004-12-21 BR BRPI0418254-5A patent/BRPI0418254A/pt not_active IP Right Cessation
-
2006
- 2006-05-25 IL IL175908A patent/IL175908A0/en unknown
- 2006-06-28 CR CR8492A patent/CR8492A/es not_active Application Discontinuation
- 2006-07-28 ZA ZA200606293A patent/ZA200606293B/xx unknown
- 2006-07-28 NO NO20063477A patent/NO20063477L/no not_active Application Discontinuation
- 2006-07-31 EC EC2006006740A patent/ECSP066740A/es unknown
-
2007
- 2007-04-17 HK HK07104008.5A patent/HK1097000A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HK1097000A1 (en) | 2007-06-15 |
JP2007516999A (ja) | 2007-06-28 |
CN100510098C (zh) | 2009-07-08 |
CN1902322A (zh) | 2007-01-24 |
ECSP066740A (es) | 2006-10-31 |
MXPA06007564A (es) | 2006-12-14 |
ZA200606293B (en) | 2009-08-26 |
DE10361794B3 (de) | 2005-10-06 |
IL175908A0 (en) | 2006-10-05 |
BRPI0418254A (pt) | 2007-04-17 |
AU2004309076A1 (en) | 2005-07-14 |
NO20063477L (no) | 2006-08-23 |
CA2546981A1 (en) | 2005-07-14 |
WO2005064006A1 (en) | 2005-07-14 |
EP2113031A1 (en) | 2009-11-04 |
CR8492A (es) | 2007-03-08 |
KR20070029641A (ko) | 2007-03-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1394157B1 (en) | Process for the preparation of 3,5-dihydroxy substituted esters as intermediates for producing optically active 2-(6-(hydroxymethyl)-1,3-dioxan-4-yl) acetic acid dervatives | |
Chai et al. | Chiral Brønsted acid-catalyzed diastereo-and enantioselective synthesis of CF 3-substituted aziridines | |
US20060246557A1 (en) | Process for preparing optically active 2-[6-(hydroxy-methyl)-1,3-dioxan-4-yl] acetic acid derivatives | |
Firouzabadi et al. | Zirconium tetrachloride (ZrCl4) catalyzed highly chemoselective and efficient acetalization of carbonyl compounds | |
RU2006127553A (ru) | Новые оптические активные, гетероароматические в-гидроксиэстеры, способы их получения из в-кетоэстеров, а также способы получения таких в-кетоэстеров | |
Drożdż et al. | Chemo-enzymatic Baeyer–Villiger oxidation in the presence of Candida antarctica lipase B and ionic liquids | |
Aratake et al. | Small organic molecule in enantioselective, direct aldol reaction “in water” | |
Tascedda et al. | Electrosynthesis of cyclic carbamates from aziridines and carbon dioxide | |
Yang et al. | Mechanisms and reactivity differences of proline-mediated catalysis in water and organic solvents | |
Zinatullina et al. | Kinetic characteristics of the reaction of natural thiols with peroxyl radicals and hydrogen peroxide | |
Terrier et al. | The levelling effect of solvational imbalances in the reactions of oximate α-nucleophiles with electrophilic phosphorus centers. Relevance to detoxification of organophosphorus esters | |
Horikoshi et al. | Selection of Microorganisms Producing Two Chiral Centers | |
JP4170221B2 (ja) | 光学活性3−ヒドロキシペンタンニトリルの製造方法 | |
JP3067817B2 (ja) | 光学活性(−)−2−ハロ−1−(置換フェニル)エタノールの製造法 | |
JP4432315B2 (ja) | 光学活性3−ヒドロキシ−3−(2’−チエニル)プロピオン酸エステル誘導体の製造方法 | |
Ohkubo et al. | High esterolytic activity of a novel water-soluble polymer catalyst imprinted by a transition-state analogue | |
JP3766465B2 (ja) | 光学活性な2級アルコールの製造法 | |
Yus | Preparation of Enantioenriched Homoallylic Primary Amines | |
US7935827B2 (en) | Optically active, heteroaromatic β-hydroxy esters and processes for their preparation from β-keto esters and processes for the preparation of these β-keto esters | |
NAKATSUKA et al. | Gly-0* Bu♦/y—> Me-^ co^ Bu-ÜÜ&+ М^ Д^ | |
RU2003125216A (ru) | Кислотный состав для обработки терригенных коллекторов и способ кислотной обработки призабойной зоны пласта | |
Yamazaki et al. | Prediction of the Optimum Reaction Time for Carbon-11 Labelling Reactions. The Rate Constants for the Carboxylation of Grignard Reagents. | |
Kocková-Kratochvílová | Urease and extracellular nucleases of yeasts | |
RU2003125214A (ru) | Кислотный состав для обработки низкопроницаемых терригенных коллекторов и способ кислотной обработки призабойной зоны пласта с его применением | |
Nakamura et al. | Asymmetric Reactions Using Optically Active β-Silyl Sulfoxides and their Application |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20090403 |