Reactions of nitro sugars. VII. A study on acetylation and some chemical properties of acetates

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Abstract
The 2,4,6-tri-O-acetates of methyl 3-deoxy-3-nitro-β-D-glucopyranoside, -galactopyranoside, and-mannopyranoside, the 2-O-acetates of the 4,6-O-benzylidene derivatives of the two first-mentioned glycosides, and the tetra-O-acetate of 1,4-dideoxy-1,4-dinitro-neo-inositol are prepared by boron trifluoride–catalyzed acetylation. The advantages of the procedure over acetylation in pyridine are pointed out. The gluco triacetate, when produced in the presence of pyridine, is accompanied by crystalline by-products of a novel nature. It suffers undetermined changes by the action of activated alumina, and in dilute aqueous alkali it is instantly converted into an unsaturated nitronate.

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