Koenigs-Knorr Synthesis of Cycloalkyl GlycosidesAuthor(s): Zdenek Wimmer | Lucie Pechova | David Saman
Journal: Molecules ISSN 1420-3049
Volume: 9; Issue: 11; Start page: 902; Date: 2004;
Keywords: Koenigs-Knorr synthesis | Cycloalkyl-ÃŽÂ²-D-glucopyranosides | Cycloalkyl-ÃŽÂ²- D-galactopyranosides | Cadmium carbonate.
Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorrsynthesis of 2-(4-methoxybenzyl)cyclohexyl-ÃŽÂ²-D-glycopyranosides. Using this promotermodel glucoside and galactoside derivatives of cyclic (i.e., secondary) alcohols weresynthesized in 50Ã¢Â€Â“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.