Stereocontrolled synthesis of 2-azido and 2-N-acetylamino-2-deoxy-β-<scp>D</scp>-C-glycosides from the corresponding lactones

Abstract

The reaction of perbenzylated 2-azido-2-deoxy-D-hexono-1,5-lactones with organometallic reagents followed by reduction provides a new stereocontrolled synthesis of 2-azido-2-deoxy-β-D-C-glycosides, which can be efficiently transformed into 2-N-acetylamino-2-deoxy-β-D-C-glycosides.