Nitrogen-Containing Carbohydrate Derivatives .X. Rearrangement Of Methyl 4,6-O-Benzylidene-3-Deoxy-3-Phenylazo-Aldohexo-Pyranosides With Alkali - A Route To Hexosid-3-Uloses

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.