Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Galactopyranoside Stereoisomers

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Title:Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Galactopyranoside Stereoisomers
Creators:
Šaman, David
Wimmerová, Martina
Wimmer, Zdeněk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 8, pp. 1186-1198
Uncontrolled Keywords:Alkyl β-D-galactopyranoside, Koenigs-Knorr synthesis, Chiral HPLC, Glycosylations, Juvenogens, Juvenoids, Glycosides, Stereoselective reactions

Abstract

Several promoters were used in the Koenigs-Knorr synthesis of the title alkyl β-D-galactopyranosides, both in their diastereoisomeric forms (<strong>5a</strong>/<strong>5b</strong> and <strong>6a</strong>/<strong>6b</strong>), resulting from the synthesis performed with the respective racemic <i>cis</i> and <i>trans</i> isomers of 2-(4-methoxybenzyl)cyclohexan-1-ol, and in their enantiomerically pure forms <strong>5a</strong> and <strong>6a</strong>, starting only from the (1<i>S</i>,2<i>S</i>)- and (1<i>S</i>,2<i>R</i>)-enantiomers of 2-(4-methoxybenzyl)cyclohexan-1-ol. The aim of the study was to find convenient modification(s) of the Koenigs-Knorr synthesis of alkyl β-D-galactopyranosides from more hindered and more complex 2-substituted cycloalkanols. Separation of the diastereoisomeric compounds using HPLC on a chiral Nucleodex-β-OH column was used to obtain small quantities of all possibly existing enantiomerically pure products for unambiguous structure assignment by NMR analysis. The (1<i>S</i>,2<i>S</i>)- and (1<i>S</i>,2<i>R</i>)- enantiomers of 2-(4-methoxybenzyl)cyclohexan-1-ol (<strong>1a</strong> and <strong>2a</strong>) were prepared by a reduction of 2-(4-methoxybenzyl)cyclohexan-1-one with <i>Saccharomyces cerevisiae</i> in enantiomeric purities: ee = 98.5% ((1<i>S</i>,2<i>S</i>)-enantiomer (<strong>1a</strong>)), and ee ≥ 99% ((1<i>S</i>,2<i>R</i>)-enantiomer (<strong>2a</strong>)). <p>

Title:Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Galactopyranoside Stereoisomers
Creators:
Šaman, David
Wimmerová, Martina
Wimmer, Zdeněk
Uncontrolled Keywords:Alkyl β-D-galactopyranoside, Koenigs-Knorr synthesis, Chiral HPLC, Glycosylations, Juvenogens, Juvenoids, Glycosides, Stereoselective reactions
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:8
Page Range:pp. 1186-1198
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061186UNSPECIFIED
ID Code:2533
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Šaman, David; Wimmerová, Martina; Wimmer, Zdeněk (2006) Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Galactopyranoside Stereoisomers. Collection of Czechoslovak Chemical Communications, 71 (8). pp. 1186-1198. ISSN 0010-0765

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