A simple and convenient synthetic protocol for O-isopropylidenation of sugars using bromodimethylsulfonium bromide (BDMS) as a catalyst.

Various O-isopropylidene derivatives of sugars and acyclic sugars were obtained in very good yields on reaction with acetone at room temperature with a catalytic amount of bromodimethylsulfonium bromide (BDMS). These O-isopropylidene derivatives can also be prepared in good yields on reaction with 2,2-dimethoxypropane (DMP) in acetonitrile using the same catalyst in shorter reaction times. Some of the advantages of this method are high effectiveness, a nonaqueous workup procedure, economic viability, and good yields. Copyright 2009 Elsevier Ltd. All rights reserved.