About: Synthesis and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers

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About: Synthesis and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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. (cs) 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. 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. (en)
Title	Synthesis and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers Syntéza a identifikace enantiomerů 2-(4-Methoxybenzyl)cyklohexyl beta-D-glukopyranosidu (cs) Synthesis and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers (en)
skos:prefLabel	Synthesis and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers Syntéza a identifikace enantiomerů 2-(4-Methoxybenzyl)cyklohexyl beta-D-glukopyranosidu (cs) Synthesis and structure assignment of 2-(4-Methoxybenzyl) cyclohexyl beta-D-Glucopyranoside enantiomers (en)
skos:notation	RIV/60461373:22330/06:00017738!RIV07-MSM-22330___
http://linked.open.../vavai/riv/strany	1470-1483
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM6046137305)
http://linked.open...iv/cisloPeriodika	10
http://linked.open...vai/riv/dodaniDat	2007
http://linked.open...aciTvurceVysledku	Moravcová, Jitka
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta potravinářské a biochemické technologie
http://linked.open...dnocenehoVysledku	502801
http://linked.open...ai/riv/idVysledku	RIV/60461373:22330/06:00017738
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	glycosides; glycosidations; glucosylations; Koenigs-Knorr synthesis; enzymatic reduction; insect juvenile hormon analogs; juvenoids; chiral HPLC; NMR spectroscopy (en)
http://linked.open.../riv/klicoveSlovo	NMR spectroscopy Koenigs-Knorr synthesis juvenoids glycosides chiral HPLC enzymatic reduction glucosylations glycosidations insect juvenile hormon analogs
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[5A308463651E]
http://linked.open...i/riv/nazevZdroje	Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...UplatneniVysledku	2006
http://linked.open...v/svazekPeriodika	71
http://linked.open...iv/tvurceVysledku	Wimmer, Zdeněk Šaman, David Moravcová, Jitka Wimmerová, Martina Kratina, Pavel
http://linked.open...n/vavai/riv/zamer	Teoretické základy potravinářských a biochemických technologií
issn	0010-0765
number of pages	14 (xsd:int)
http://localhost/t...ganizacniJednotka	22330

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