Synthesis of the (1R,2S)-stereoisomers of the respective E- and Z-isomers of ethyl 4-[(2-hydroxycyclohexyl)methyl]phenoxy-3-methyl-2-butenoate using yeast whole cell bioreduction of the parent ketones
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F05%3A00021178" target="_blank" >RIV/61388963:_____/05:00021178 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
Synthesis of the (1R,2S)-stereoisomers of the respective E- and Z-isomers of ethyl 4-[(2-hydroxycyclohexyl)methyl]phenoxy-3-methyl-2-butenoate using yeast whole cell bioreduction of the parent ketones
Original language description
Saccharomyces cerevisiae, strain DBM 2115, was successfully employed in the reduction of the separated Z- and E-isomers of ethyl 4-[(2-oxocyclohexyl)methyl]phenoxy-3-methyl-2-butenoates 1 and 2, in order to prepare the (1S,2S)- and (1R,2S)-enantiomers ofthe corresponding ethyl 4[(2-hydroxycyclohexyl)methyl]phenoxy-3-methyl-2-buteonates 3-6. The products were obtained with the required absolute configuration: (1S,2S)-3 (ee=98%; yield 48%), (1R,2S)-4 (ee=>99%; yield 45%), (1S,2S)-5 (ee=98.5%; yield 47%),and (1R,2S)-6 (ee=>99%; chemical yield 44%).
Czech name
Synthesa (1S,2S)- a (1R,2S)-stereoisomerů E a Z isomerů ethyl 4-[(2-hydroxycyklohexyl)methyl]fenoxy-3-methyl-2-butenoátu za použití bioredukce mateřského ketonu celými buňkami kvasinky
Czech description
Saccharomyces cerevisiae, kmen DBM 2115, byl úspěšně použit při redukci Z a E isomerů ethyl 4-[(2-oxocyklohexyl)methyl]fenoxy-3-methyl-2-butenoátu (1 a 2), za účelem přípravy (1S,2S) a (1R,2S) enantiomerů odpovídajícího ethyl4-[(2-hydroxycyklohexyl)methyl]fenoxy-3-methyl-2-butenoátu (3-6). Produkty byly získány s požadovanou absolutní konfigurací: 3 (ee=98%; chemický výtěžek 48%), 4(ee=>99%; chemický výtěžek 45%), 5(ee=98.5%; chemický výtěžek 47%) and 6(ee=>99%; chemický výtěžek 44%).
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/OC%20D29.001" target="_blank" >OC D29.001: Sustainable Design of Biologically Important Agens</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2005
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Tetrahedron Asymmetry
ISSN
0957-4166
e-ISSN
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Volume of the periodical
16
Issue of the periodical within the volume
16
Country of publishing house
GB - UNITED KINGDOM
Number of pages
16
Pages from-to
2810-2815
UT code for WoS article
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EID of the result in the Scopus database
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