Synthesis of 2,3:4,6-di-O-isopropylidene-D-allopyranose from D-glucose

Carbohydr Res. 2005 Aug 15;340(11):1872-5. doi: 10.1016/j.carres.2005.05.011.

Abstract

2,3:4,6-Di-O-isopropylidene-d-allopyranose can be conveniently prepared from d-glucose via a synthetic sequence, which includes Mitsunobu inversion at O-3, di-O-isopropylidenation of phenyl-1-thio-d-alloside and anomeric deprotection on treatment with NBS/CaCO3.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrates / chemistry
  • Disaccharides / chemistry
  • Glucose / chemistry*
  • Glycosides / chemistry
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Hexoses / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Oligosaccharides / chemistry
  • Temperature

Substances

  • 2,3-4,6-di-O-isoopropylideneallopyranose
  • Carbohydrates
  • Disaccharides
  • Glycosides
  • Heterocyclic Compounds, 3-Ring
  • Hexoses
  • Oligosaccharides
  • Glucose