Nitrogen-containing carbohydrate derivatives. Part X. Rearrangement of methyl 4,6-O-benzylidene-3-deoxy-3-phenylazo-aldohexopyranosides with alkali: a route to hexosid-3-uloses

Abstract

The opening of the epoxide ring in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannoside with phenylhydrazine, followed by oxidation of the product, has given methyl 4,6-O-benzylidene-3-deoxy-3-phenylazo-α-D-altroside. This compound and the α-gluco- and β-galacto-analogues have been rearranged by base to the corresponding 3-phenylhydrazones, which in turn have been converted into the parent hexosid-3-uloses, thus providing a new route to these compounds.