Per-O-Benzylated Ethyl 5-N-Acetyl-α-thiosialoside as a Glycosyl Donor for α-Silylation

Abstract

Per-O-benzylated ethyl 5-N-acetyl-α-thiosialoside 1 was synthesized and its reactivity as a sialyl donor was investigated. It was demonstrated that the reactions of 1 with various primary and secondary alcohol acceptors, including monosaccharides, gave good to excellent yields (53-92%) and acceptable to excellent α-selectivity (α:β = 2 ∼ 10:1) , showing its promise for application to sialoglycan synthesis.