Protic Acid (HClO₄ Supported on Silica Gel)-Mediated Synthesis of 2,3-Unsaturated-<i>O</i>-glucosides and a Chiral Furan Diol from 2,3-Glycals

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.