Collect. Czech. Chem. Commun. 1979, 44, 2526-2535

Preparation of 6-amino-6-deoxy-D-allonic and 6-amino-6-deoxy-D-gluconic acid

Karel Kefurt, Karel Čapek, Zdeňka Kefurtová and Jiří Jarý

Laboratory of Monosaccharides, Prague Institute of Chemical Technology, 166 28 Prague 6


Partial tosylation of monoisopropylidene glucose I and monoisopropylidene allose II gave their 6-O-tosyl derivatives III and IV which were further converted to 6-azido-6-deoxy-D-glucose (XV ) and 6-azido-6-deoxy-D-allose (XVI) via 5,6-anhydrocompounds XII and X as intermediates. Oxidation of the products gave corresponding lactones XVIII and XVII. On their catalytic hydrogenation in methanol lactams XXII and XXI were prepared, while hydrogenation in water gave 6-amino-6-deoxy-D-allonic (XXIII) and 6-amino-6-deoxy-D-gluconic (XXIV) acids.