T. Sakakibara, Y. Nomura, R. Sudoh
Jun 1, 1980
Citations
0
Influential Citations
12
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The title compound was synthesized from 1,5-anhydro-D-glucitol via nitromethane cyclization. The reduction of the compound with sodium borodeuteride afforded a mixture of saturated nitro compounds having an axial and equatorial deuterium atom at C-2 in an approximate ratio of 2:1. On the other hand, the reaction with hydrogen cyanide gave predominantly the adduct with the manno configuration, together with small amounts of a cyano olefin. The reaction with hydrazoic acid yielded addition products with the gluco and manno configurations; the ratio was strongly affected by the solvent used.