Highly Stereoselective Synthesis of 2-Amino-3-C-methyl-2,3-dideoxyaldoses by C_3-Chain Elongation via Homoaldol Reaction of Sugar Aldehydes

摘要

A flexible strategy for the stereoselective synthesis of branched amino sugar analogues is described. It is based on a C3-chain elongation of suitable protected aldoses. By using the sequence homoaldol reaction, epoxidation, and methanolysis a-meth-yl a//o-furanosides are obtained. Proximate amination of the corresponding triflates afford the title compounds. All reactions proceed with high yield, high diastereoselectivities, and allow for a broad application.