The Aldosyl Azides

The aldosyl azides resemble the aldosyl halides, especially the fluorides this is to be expected from the similarities of hydrazoic acid and the halogen 

The first poly-O-acetylaldosyl azide was synthesized by Bertho by treating tetra-O-acetyl-a-D-glucopyranosyl bromide with a metal azide. In addition to the aldosyl azide derivatives that are known (see Table IV), derivatives of 2-amino-2-deoxy-D-glucosyl azide have been prepared - (see Table V). If the trans hydroxyl group at C-2 is not acetylated, an intermediate epoxide of the type suggested for the aldosyl fluorides can form, and the azide obtained has the. same anomeric configuration as the original halide, as. shown by the formulas. The acetylated azides, like the 

Reduction of the acetylated aldosyl azides affords the corresponding acetylated aldosylamines, as exemplified by the preparation of lri-0-acetyl-2-amino-2-deoxy-j8-D-glucopyranosylamine (31 33). 

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