SYNTHESIS OF 4-ACETAMIDO-4-DEOXY-SUGARS

Abstract

The tri-O-methanesulfonate derivative (I) of methyl α-D-xylopyranoside has been prepared. This compound when heated with sodium azide in N,N-dimethylformamide yielded a 4-azido derivative with inversion at C4. It (I) was thus converted to a methyl 4-azido-4-deoxy-β-L-arabinopyranoside (II) and thence by removal of methanesulfonate residues to a 2,3-anhydro-L-ribopyranoside derivative and further to methyl 4-amino-4-deoxy-β-L-xylopyranoside (V); 4-acetamido-4-deoxy-1,2;3,5-di-O-isopropylidene-L-xylose (IX), a sugar with nitrogen in the ring, was prepared from 4-acetamido-4-deoxy-L-xylose. Acetolysis of methyl 4-acetamido-4-deoxy-L-xylopyranoside yielded a pentacetate of unknown ring size (X or XI).