SYNTHESIS OF 6-AMINO-1,6-ANHYDRO-6-DEOXYSUGAR DERIVATIVES

Staudinger reaction of triphenylphosphine with O-acetyl-6-O-p-tolylsul fonyl-beta-D-glycopyranosyl azides led to an anomeric iminophosphorane which rearranged in situ by elimination of the sulfonate at C-6. The xy-6-triphenylphosphonioamino-beta-D-glycopyranose salts thus obtained were transformed into the corresponding 6-amino-1,6-anhydro-6-deoxy-b eta-D-glycopyranosesa which were further N-acylated or N-alkoxycarbony lated. H-1 and C-13 NMR of these products show the occurrence of two r otamers in solution, due to restricted rotations around the amide bond (C) 1998 Elsevier Science Ltd. All rights reserved.