Cyclitols. XXXI. Synthesis of Amino- and Nitro-cyclopentanetetrols

Abstract

Condensation of 2,3-O-cyclohexylidene-erythro-tetrodialdose with nitromethane gave a mixture of diastereomers of 2,3-O-cyclohexylidene-5-nitro-1,2,3,4-cyclo-pentanetetrol, one of which was isolated. After hydrogenation of the mixture, (1,4,5/2,3)- and (1,4/2,3,5)-5-amino-2,3-O-oyclohexylidene-l,2,3,4-cyclopentanetetrol were isolated, the latter conveniently as its condensation product with acetone. Deamination of the 1,4/2,3,5 compound gave an epoxide (8). Heating the nitro compounds with sodium hydrogen carbonate in methanol caused methylation of the two hydroxyl groups.