Koenigs-Knorr synthesis of cycloalkyl glycosides

Molecules. 2004 Nov 30;9(11):902-12. doi: 10.3390/91100902.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Hydrocarbons, Cyclic / chemical synthesis*
  • Hydrocarbons, Cyclic / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Glycosides
  • Hydrocarbons, Cyclic