Stereoselective synthesis of conformationally constrained cyclohexanediols: a set of molecular scaffolds for the synthesis of glycomimetics

J Org Chem. 2001 Sep 21;66(19):6209-16. doi: 10.1021/jo015570b.

Abstract

The practical, stereoselective synthesis of the three diastereoisomeric 1,2-trans-dicarboxy-4,5-cyclohexanediols 1-3 (DCCHDs) is described, starting from a common precursor, easily available in both enantiomeric forms. The regioselective derivatization of all functional groups of 1 is also reported. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclohexanols / chemical synthesis*
  • Cyclohexanols / chemistry*
  • Drug Design
  • Molecular Conformation
  • Molecular Mimicry*
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry*

Substances

  • Cyclohexanols
  • Monosaccharides