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Koenigs-Knorr Synthesis of Cycloalkyl Glycosides

Author(s): Zdenek Wimmer | Lucie Pechova | David Saman

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 11;
Start page: 902;
Date: 2004;
Original page

Keywords: Koenigs-Knorr synthesis | Cycloalkyl-β-D-glucopyranosides | Cycloalkyl-β- D-galactopyranosides | Cadmium carbonate.

Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorrsynthesis of 2-(4-methoxybenzyl)cyclohexyl-β-D-glycopyranosides. Using this promotermodel glucoside and galactoside derivatives of cyclic (i.e., secondary) alcohols weresynthesized in 50–60 % overall yields. Diastereoisomeric mixtures of products wereobtained in these syntheses, which started from racemic isomers of 2-(4-methoxy-benzyl)cyclohexanol. The prepared compounds have been purified and characterized bytheir 1H- and 13C-NMR spectra, as well as by their IR and MS spectra, in order to usethem as reference compounds in planned subsequent research.
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