Regioselective one pot approach to aminodeoxy sugars via aminosilanes

Abstract

A novel one-step synthesis of regioisomerically pure aminodeoxy sugars (6)–(11) has been achieved by trans-diaxial cleavage of the oxirane ring in 2,3-anhydro sugars (1)–(5) with N,N-diethyltrimethylsilylamine or its N,N-dimethyl analogue, using AlCl₃ as catalyst; the reagents work under mild conditions and avoid the difficulties which sometimes are encountered in ring-opening reactions of epoxy sugars.