Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Glucopyranoside Enantiomers

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Title:Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Glucopyranoside Enantiomers
Creators:
Šaman, David
Kratina, Pavel
Moravcová, Jitka
Wimmerová, Martina
Wimmer, Zdeněk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 10, pp. 1470-1483
Uncontrolled Keywords:Koenigs-Knorr synthesis, Chiral HPLC, Glycosidations, Glucosylations, Juvenoids, Enzymatic reduction, Insect juvenile hormon analogs, Glycosides, NMR spectroscopy

Abstract

Glucosylation of the <i>cis</i>- and <i>trans</i>-isomers of 2-(4-methoxybenzyl)cyclohexan-1-ol (<strong>1a</strong>/<strong>1b</strong>, <strong>2a</strong>/<strong>2b</strong>, <strong>1a</strong> or <strong>2a</strong>) was performed to prepare the corresponding alkyl β-D-glucopyranosides, mainly to get analytical data of pure enantiomers of the glucosides (<strong>3a</strong>-<strong>6b</strong>), required for subsequent investigations of related compounds with biological activity. One of the employed modifications of the Koenigs-Knorr synthesis resulted in achieving 85-95% yields of&nbsp;pure β-anomers <strong>3a</strong>/<strong>3b</strong>, <strong>4a</strong>/<strong>4b</strong>, <strong>3a</strong> or <strong>4a</strong> of protected intermediates, with several promoters and toluene as solvent, yielding finally the deprotected products <strong>5a</strong>/<strong>5b</strong>, <strong>6a</strong>/<strong>6b</strong>, <strong>5a</strong> or <strong>6a</strong> as pure β-anomers. To obtain enantiomerically pure β-anomers of the target structure (<strong>3a</strong>, <strong>4a</strong>, <strong>5a</strong> and <strong>6a</strong>) for unambiguous structure assignment, an enzymic reduction of 2-(4-methoxybenzyl)cyclohexan-1-one by <i>Saccharomyces cerevisiae</i> whole cells was performed to get (1<i>S</i>,2<i>S</i>)- and (1<i>S</i>,2<i>R</i>)-enantiomers (<strong>1a</strong> and <strong>2a</strong>) of 2-(4-methoxybenzyl)cyclohexan-1-ol. The opposite enantiomers of alkyl β-D-glucopyranosides (<strong>5b</strong> and <strong>6b</strong>) were obtained by separation of the diastereoisomeric mixtures <strong>5a</strong>/<strong>5b</strong> and <strong>6a</strong>/<strong>6b</strong> by chiral HPLC. All stereoisomers of the products (<strong>3a</strong>-<strong>6b</strong>) were subjected to a detailed <sup>1</sup>H NMR and <sup>13</sup>C NMR analysis. <p>

Title:Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Glucopyranoside Enantiomers
Creators:
Šaman, David
Kratina, Pavel
Moravcová, Jitka
Wimmerová, Martina
Wimmer, Zdeněk
Uncontrolled Keywords:Koenigs-Knorr synthesis, Chiral HPLC, Glycosidations, Glucosylations, Juvenoids, Enzymatic reduction, Insect juvenile hormon analogs, Glycosides, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:71
Number:10
Page Range:pp. 1470-1483
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061470UNSPECIFIED
ID Code:2555
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Šaman, David; Kratina, Pavel; Moravcová, Jitka; Wimmerová, Martina; Wimmer, Zdeněk (2006) Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Glucopyranoside Enantiomers. Collection of Czechoslovak Chemical Communications, 71 (10). pp. 1470-1483. ISSN 0010-0765

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