Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals

J Org Chem. 2004 Sep 3;69(18):6137-40. doi: 10.1021/jo049415j.

Abstract

Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good alpha selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calcium Gluconate / chemistry
  • Catalysis
  • Galactose / analogs & derivatives*
  • Galactose / chemistry
  • Glucosides / chemical synthesis*
  • Indicators and Reagents
  • Molecular Structure
  • Perchlorates / chemistry*
  • Silica Gel
  • Silicon Dioxide / chemistry*

Substances

  • Glucosides
  • Indicators and Reagents
  • Perchlorates
  • galactal
  • Silica Gel
  • Silicon Dioxide
  • Calcium Gluconate
  • Galactose