Crystal structure of 3,4,5,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucose (4- nitrophenyl)-hydrazon, C20H24N6O10

The p-nitrophenyl hydrazon moiety of per-0-acetylated aldoses exhibited similar but weaker activating effect (see ref. 1) for the nucleophilic replacement of AcO-2 than related formazyl group (see refs. 2-4). Treatment of 2,3,4,5,6-penta-O-acetyl-D-glucose (4-nitrophenyl)-hydrazon with sodium azide afforded the title compound and the mannose epimer which were separated by column chromatography (see ref. 1). Evidences for the structure of the two products were obtained by ' h and C NMR spectroscopy but leaving the assignment of the configuration of C-2 of each acyclic sugar chain uncertain. The gluco configuration of the title compound was proved by X-ray crystallography.