Synthesis of Potential Antimicrobial Agents from Maltose. III. Introduction of an Amino Group Into the 3′-Position of 1,6-Anhydro-Disaccharides

Abstract

Regioselective cleavage of 1,6-anhydro-maltose (1) with periodate and the subsequent recyclization with nitromethane gave 1,6-anhydro-3''-deoxy-3''-nitrodisaccharides (3). Three diastereomers, prepared by benzylidenation of 3, were separated by column chromatography. Each of 4'', 6''-0-benzylidene derivatives successively underwent debenzylidenation, reduction of the nitro group and peracetylation to give 3''-acetamido-3''-deoxy-disaccharide derivatives (7, 8 and 9). The configurations of the 3-amino sugar moieties in 7 (D-gluco), 8 (D-manno) and 9 (D-galacto) were determined on the basis of the 1H NMR data. The main product (7) was further modified to the 6-deoxy-6-nitro derivative.