Abstract
Abstract Staudinger reaction of triphenylphosphine with 2,3,4-tri- O -acetyl-6- O - p -tolylsulfonyl- β - d -glycopyranosyl azides led to an anomeric iminophosphorane which rearranged in situ by elimination of the sulfonate at C-6. The 1,6-anhydro-6-deoxy-6-triphenylphosphonioamino- β - d -glycopyranose salts thus obtained were transformed into the corresponding 2,3,4-tri- O -acetyl-6-amino-1,6-anhydro-6-deoxy- β - d -glycopyranoses which were further N -acylated or N -alkoxycarbonylated. 1 H and 13 C NMR of these products show the occurrence of two rotamers in solution, due to restricted rotations around the amide bond.
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