Nitrogen-containing carbohydrate derivatives. Part XI. Reduction of methyl 4,6-O-benzylidene-α-D-hexosid-3-ulose phenylhydrazones

Abstract

Hydrogenation of methyl 4,6-O-benzylidene-α-D-ribo-hexosid-3-ulose phenylhydrazone and its arabino-isomer with Raney nickel gave methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-alloside and the corresponding 3-amino-altroside, respectively. Reduction with lithium aluminium hydride followed by oxidation with mercuric oxide gave predominantly the 3-phenylazo-gluco- and altro-compounds, respectively.