Stereoselective synthesis of glycoclusters using an olefin metathesis and Sharpless dihydroxylation sequence

An asymmetric synthesis of α-d-mannopyranoside-based glycoclusters has been accomplished using olefin metathesis and Sharpless asymmetric dihydroxylation reactions as key steps. Access to a family of dimeric and tetrameric glycoclusters having chiral core structures was achieved to investigate topographical arrays of carbohydrate–protein binding interactions.