Glucose phenylosotriazole

The action of lead tetraacetate on osazones of Cw-labeled sugars in warm aqueous acetic acid has been employed46 for determining specific activity of the oxidizable carbon atoms present, that is, C4, C5, and C6 of D-glucose phenylosotriazole. In the potassium acetate-catalyzed oxidation, D-glucos-azone (o-arabino-hexose phenylosazone) yielded two moles of formic acid... 

Another degradation product which throws light on the structure of n-glucose phenylosotriazole is 2-phenyl-l,2,3-triazole-4-carboxylic acid (5), obtained when n-glucose phenylosotriazole (2) is oxidized with 20% nitric acid, aqueous potassium permanganate, or ceric sulfate. This acid had also been prepared by von Pechmann from treatment of 4-methyl-2-phenyl-l, 2,3-triazole (6) with alkaline potassium permanganate. 

Boiling a solution of sugar phenylosotriazoles in methanolic sulfuric acid causes the elimination of water and formation of a 3,6-anhydro ring, with a partial Walden inversion at C-3. Thus, n-am mo-hexose ( n-glucose ) phenylosotriazole (2) yields a mixture of D-ara6zno-hexose ( n-glucose ) and n-n to-hexose ( n-allose ) 3,6-anhydrophenylosotria-zoles (12) and (13), respectively. - Similarly, L-xi/lo-hexose phenylosotriazole afforded 3,6-anhydro-D-Z /a o-hexose phenylosotriazole. ... 

On oxidation of the phenylosotriazole derivative of the disaccharide with sodium periodate, three moles of periodate are consumed with the formation of one mole each of formic acid and formaldehyde per mole of the phenylosotriazole derivative. If the D-glucose in the u-glucopyrano-syl-L-arabinose phenylosotriazole were attached to carbon atom 4 of the L-arabinose derivative, oxidation of this compound with sodium periodate would require two moles of periodate and would liberate one mole of... 

Bevington and coworkers have suggested a scheme for determining the distribution of radioactive carbon in labeled n-glucose, using the degradation of D-arabino-hexose phenylosotriazole. The scheme is based on the periodate oxidation of n-ambmo-hexose phenylosotriazole and d-arabino-hexose phenylosotriazole 6-benzoate. The former gives formaldehyde from C-6, formic acid from C-4 and C-5, and 4-formyl-2-phenyl-1,2,3-triazole from C-1, C-2, and C-3. This latter aldehyde can be further... 

---