Stereoselective synthesis of α-glucosides from 3-O-propargyl protected glucal exploiting the alkynophilicity of AuCl3

The stereoselective synthesis of 2,3-unsaturated alpha-D-glucosides by the S(N)2' addition of diverse aglycones onto 4,6-di-O-benzyl-3-O-propargyl glucal was achieved using a catalytic quantity of AuCl3. The Au catalyzed reaction was explored using various aliphatic, aromatic, alicyclic and monosaccharide aglycones. The current protocol tolerates diverse functional groups and is highly stereoselective, fast, catalytic and mild. (c) 2006 Elsevier Ltd. All rights reserved.