Koenigs-Knorr synthesis of cycloalkyl glycosides

Abstract

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