HETEROCYCLIC AMINO SUGAR DERIVATIVES .I. DERIVATIVES OF 2-AMINO-2-DEOXY-D-ALLOPYRANOSE

A facile synthetic route from D-glucosamine to benzyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (VIII) was developed. A number of D-allosamine derivatives were prepared for characterization. Reaction of benzyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (VIII) with phosgene, diphenylcarbonate, N,N′-carbonyldiimidazole, or hexachloroacetone gave benzyl 4,6-O-benzylidene-β-D-allopyranosido[2,3:4′,5′]-2′-oxazolidone (X) in excellent yield. A new method developed in this investigation is the utilization of hexachloroacetone to prepare a N-trichloroacetamido compound which is subsequently cyclized to give 2-oxazolidone X. © 1969, American Chemical Society. All rights reserved.