A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols

J Org Chem. 2005 Nov 25;70(24):10099-101. doi: 10.1021/jo051566e.

Abstract

[reaction: see text] A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry*
  • Glycols / chemical synthesis*
  • Glycols / chemistry
  • Molecular Conformation
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Carbohydrates
  • Glycols