Synthesis of 2-amino-2-deoxy-D-hexopyranosides from 4-O-trichloroacetimidyl-D-hex-2-enopyranoside by [3,3]-sigmatropic rearrangement

Abstract 2-Amino-2-deoxysugars, D -mannosamine and D -altrosamine derivatives were synthesized together with D -idosamine and D -talosamine ones from a 2-deoxy-2-trichloroacetamido-hex-3-enopyranoside. This key intermediate was prepared by regio- and stereoselective [3,3]-sigmatropic rearrangement of 4- O -trichloroacetimidyl-hex-2-enopyranoside.