Abstract
Acyl nitrites, either preformed or generated in situ, add to 3,4,6-tri- O-acetyl- d-glucal in a cis fashion to give dimeric 2-deoxy-2-nitroso adducts having the α- d- gluco configuration. Adducts of acetyl, benzoyl, phenylacetyl, and propionyl nitrite were obtained. Partial, catalytic hydrogenation, or reduction with sodium hydrosulfite, afforded the corresponding azoxy derivatives. Prolonged reduction with a zinc-copper couple in acetic acid, followed by acetylation, and hydrolysis with sodium methoxide in methanol, gave 2-acetamido-2-deoxy- d-glucose.
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