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Molecules 2004, 9(11), 902-912; doi:10.3390/91100902
Article

Koenigs-Knorr Synthesis of Cycloalkyl Glycosides

1,* , 2 and 1
Received: 14 September 2004 / Accepted: 4 October 2004 / Published: 30 November 2004
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Abstract

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.
Keywords: Koenigs-Knorr synthesis; Cycloalkyl-β-D-glucopyranosides; Cycloalkyl-β- D-galactopyranosides; Cadmium carbonate. Koenigs-Knorr synthesis; Cycloalkyl-β-D-glucopyranosides; Cycloalkyl-β- D-galactopyranosides; Cadmium carbonate.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Wimmer, Z.; Pechova, L.; Saman, D. Koenigs-Knorr Synthesis of Cycloalkyl Glycosides. Molecules 2004, 9, 902-912.

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