Advances in Carbohydrate Chemistry, Vol. 3 by W.W. Pigman, M.L. Wolfrom, Stanley Peat (Eds.)

By W.W. Pigman, M.L. Wolfrom, Stanley Peat (Eds.)

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IV. Anhydi ides of Orazones and Hydrazoncs.. . . . . . 1. Anhydrides Prepared Directly from the Corrcsponding Osazones . , . 2. Anhydrides Prepared by the Deacetylation of Acetates. . . . . . . 3. Disaccharide Anhydro-osazones. . . . . . . . . . . . . . . . . 4. D-Mannose Anhydrophenylhydrazone Tetraacetate. . . . . . . . . V. Three Important Reactions of Osazones.. . . . . . . . . . . . . . . . 1. Convereion of Osazoncs into Osotriazoles.

Since that time the derivatives obtained by condensing sugars with phenylhydrazine and other substituted hydrazines have been used widely for purposes of identification and, in some cases, for the estimation and separation of sugars. With a few exceptions, however, it is only comparatively recently that attempts have been made to decide the precise structures of sugar hydrazones and osazones or that much attention has been given to the behavior of such compounds as chemical individuals. For that reason finality has only been reached on a few points and this review must therefore be considered as a progress report intended to show the general trend of work in this field.

The crystalline (‘a”pentaacetate was formulated as the cyclic compound 111, although it should be noted th at the assignment of a furanose ring is without experimental justification, and th at the stereochemical arrangement of the HC=NNHCsHs H&OH ! H-NH N AcC gH I 6 HCOAc HobH AcdH I HCOH I HA0 H C - HAOH HAOH HCOAc h20H I h,OH I ClH*OAc I1 I11 hydrazide group is left undecided. Treatment with benzaldehyde and potassium hydroxide gave benzaldehyde acetylphenylhydrazone and hydrolysis with hydrochloric acid gave a-acetylphenylhydrazine.

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