CYCLIZATIONS OF DIALDEHYDES WITH NITROMETHANE: XIII. SYNTHESIS OF TREHALOSE-TYPE DISACCHARIDES CONTAINING NITROGENOUS HEPTULOSES

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Abstract
The dialdehyde II that arises from a partial lead tetraacetate cleavage of sucrose has been cyclized with nitromethane to give a stereoisomeric mixture of nitro disaccharides IV via their sodium nitronates III. Upon catalytic hydrogenation a single amino disaccharide, α-D-gluco-pyranosyl 4-amino-4-deoxy-β-D-gluco-heptulopyranoside hydrochloride (V), was isolated. Various derivatives of the nitrogenous heptulose components of IV and V were prepared by methanolysis and hydrolysis. The configuration of V was established by a degradation of its its N-acetylated hydrolysis product, 4-acetamido-4-deoxy-α-D-gluco-heptulose (VII), which gave 2-amino-2-deoxy-D-arabinose hydrochloride, and by reduction of VII, which gave the two epimeric acetamido heptitols XIII and XIV.

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