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Koenigs-Knorr Synthesis of Cycloalkyl Glycosides
Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo namesti 2, CZ-16610, Prague 6, Czech Republic
Institute of Chemical Technology, Technicka 5, CZ-16028 Prague 6, Czech Republic
* Author to whom correspondence should be addressed.
Received: 14 September 2004; Accepted: 4 October 2004 / Published: 30 November 2004
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.
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Cite This Article
MDPI and ACS Style
Wimmer, Z.; Pechova, L.; Saman, D. Koenigs-Knorr Synthesis of Cycloalkyl Glycosides. Molecules 2004, 9, 902-912.
Wimmer Z, Pechova L, Saman D. Koenigs-Knorr Synthesis of Cycloalkyl Glycosides. Molecules. 2004; 9(11):902-912.
Wimmer, Zdenek; Pechova, Lucie; Saman, David. 2004. "Koenigs-Knorr Synthesis of Cycloalkyl Glycosides." Molecules 9, no. 11: 902-912.