SYNTHESIS OF 4-ACETAMIDO-4-DEOXY-SUGARS

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 C 4 . 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).