Ring-opening reactions of iminosugar-derived aziridines: application to the general synthesis of α-1- C-substituted derivatives of fagomine

Abstract

A general approach to α-1- C-substituted derivatives of fagomine (2-deoxynojirimycin-α- C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is reported. The nine-step reaction sequence proceeded in an overall yield of 14–28% from tri- O-benzyl- d-glucal. In the course of this study, the synthesis of α-1- C-ethyl-fagomine as well as of 1, N-anhydro derivatives of fagomine has been achieved for the first time.