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

The stereoselective synthesis of 2,3-unsaturated α-d-glucosides by the S_N2′ 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.