Studies of Aminosugars. XIV. Syntheses of 6,6′-Diamino-6,6′-dideoxymaltosylamine, 1′,6,6′-Triamino-,1′,6,6′-trideoxysucrose and 6,6′-Diamino-6,6′-dideoxytrehalose

Several aminodisaccharides have been synthesized for the investigation of the relationship between the structural and biochemical characteristics of aminoglycosides. The preferential tosylation of maltose, followed by acetylation and bromination, yielded 2,2′,3,3′,4′-penta-O-acetyl-6,6′-di-O-tosylmaltosyl bromide, of which the bromine atom and the two tosyloxy groups were replaced by azido groups. The removal of acetyl groups and the catalytic hydrogenation of the azido groups gave 6,6′-diamino-6,6′-dideoxymaltosylamine. By an analogous procedure, 1′,6,6′-triamino-1′,6,6′-trideoxysucrose was prepared from sucrose via 2,2′,3,3′, 4,4′-penta-O-acetyl-1′,6,6′-triazido-1’,6,6′-trideoxysucrose. 6,6′-Diamino-6,6′-dideoxytrehalose was obtained by the ammonolysis of 2,2′,3,3′,4,4′-hexa-O-acetyl-6,6′-di-O-tosyltrehalose.