Stereoselective synthesis, structural characterization, and properties of 1,2-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose

Bioorg Med Chem. 2005 Jan 17;13(2):353-61. doi: 10.1016/j.bmc.2004.10.023.

Abstract

1,2:4,5-Di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose 14 was synthesized stereoselectively from 1,2:4,5-di-O-isopropylidene-3-C-amidoximino-3-O-benzoyl-beta-D-psicopyranose 8 using a novel procedure. Treatment of 8 with acetic anhydride, chloroacetyl chloride, propanic anhydride, or benzoyl chloride causes the 3-O-benzoyl group to undergo an intramolecular replacement reaction with neighboring group participation and transfer resulting in a more stable conjugation system of the 1,2,4-oxadiazol ring. A possible mechanism, as well as structural analysis and bioactivity are described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Models, Molecular
  • Molecular Structure
  • Monosaccharides / chemical synthesis
  • Monosaccharides / chemistry*
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry*
  • Pyrans / chemistry*

Substances

  • 1,2-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose
  • Monosaccharides
  • Oxadiazoles
  • Pyrans