Synthesis and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F06%3A00017738" target="_blank" >RIV/60461373:22330/06:00017738 - 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 and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers
Original language description
Glucosylation of the cis- and trans-isomers of 2-(4-methoxybenzyl)cyclohexan-1-ol was performed by modified Koenigs-Knorr method with several promoters and toluene as solvent. Pure beta-D-glukopyranosides were obtained in 85-95% yields. To obtain enantiomerically pure beta-anomers of the target structure Saccharomyces cerevisiae whole cells was performed to get (1S,2S)- and (1S,2R)-enantiomers of starting 2-(4-ethoxybenzyl)cyclohexan-1-ol. The opposite enantiomers were obtained by separation of the diastereoisomeric mixtures by chiral HPLC. All stereoisomers of the products were subjected to a detailed 1H NMR and 13C NMR analysis.
Czech name
Syntéza a identifikace enantiomerů 2-(4-Methoxybenzyl)cyklohexyl beta-D-glukopyranosidu
Czech description
2-(4-Methoxybenzyl)cyklohexyl-beta-D-glucopyranosidy byly získány Koenigs-Knorrovou reakcí s různými promotory v toluenu ve výtěžku 85 - 95 %. Celé buňky Saccharomyces cerevisiae byly použity k stereoselektivní redukci a tím k rozdělení (1S,2S)- and (1S,2R)-enantiomerů výchozího 2-(4-methoxybenzyl)cyclohexan-1-olu, které byly glykosylovány vypracovanou metodou. Další dva enantiomerně čisté glykosidy byly připraveny separací směsi chirální HPLC. Všechny stereoisomery byly identifikovány 1H a 13C NMR.
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
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2006
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Collection of Czechoslovak Chemical Communications
ISSN
0010-0765
e-ISSN
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Volume of the periodical
71
Issue of the periodical within the volume
10
Country of publishing house
CZ - CZECH REPUBLIC
Number of pages
14
Pages from-to
1470-1483
UT code for WoS article
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EID of the result in the Scopus database
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