Stereoselective synthesis of 2-amino-2-deoxysugars: N-alkyl-D-allosamines

Stereoselective synthesis of N-alkyl-D-allosamines, designed for the preparation of N-alkyl derivatives of allosamidin (a chitinase inhibitor), is achieved by a 'carbonyl group transfer' reaction followed by stereoselective reduction and this method represents the first example of N-alkyl-D-allosamines synthesized from a 2-oxosugar.