Koenigs-Knorr synthesis of cycloalkyl glycosides.
Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorr synthesis of 2-(4-methoxybenzyl)cyclohexyl-beta-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-methoxy-benzyl)cyclohexanol. The prepared compounds have been purified and characterized by their (1)H- and (13)C-NMR spectra, as well as by their IR and MS spectra, in order to use them as reference compounds in planned subsequent research.
Wimmer
Zdenek
Z
Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo namesti 2, CZ-16610, Prague 6, Czech Republic. wimmer@uochb.cas.cz
Pechová
Lucie
L
Saman
David
D
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D006027:Glycosides; D006844:Hydrocarbons, Cyclic