Stereospecific Synthesis of the α- and β-d-Glucopyranosyl Ureas

Abstract

A new, one-pot, two-stage procedure for the preparation of the α- and β-d-glucopyranosyl ureas has been developed. Oxidation of glucopyranosyl isocyanides provides glucopyranosyl isocyanates, which can be trapped in situ with amines to afford good yields of glucopyranosyl ureas. Application of this method establishes the successful synthesis of the hitherto unknown N,N‘-di-α,α- and α,β-d-glucopyranosyl ureas.