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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OH)I XXXVIII aldehydo-n-Apiose By present conventions of nomenclature the mechanical model of apiose may be designated 3-bis(C-hydroxymethy1)-D-glyceraldehyde,and it is to be noted that only one asymmetric carbon atom is present in XXXVIII. The structure is not capable of assuming a pyranose ring but it can conceivably pass t o tautomeric forms having the furanose ring and containing three asymmetric carbon atoms. There are four such configurations and they constitute the a and /3 anomers, respectively, of two different sugars, one of which is a 3-C-hydroxymethyl-~-erythrose and the other a 3-C-hydroxymethyl-~-threose.

11. Sugar Hydrazones . . . . . . . . . . . . . . . . . . . . . . . . . . I. The D-Glucose Phenylhydrazones.. . . ........ 2. The D-Fructose Methylphenylhydrazones. . . . . . . . . . . . . 3. The Acyclic Hydrazones of D-Galactose.. . . . . . . . . . . . . 4. Optical Properties of Sugnr Hydrazones.. . . . . . . 111. Structural Studies on Sugar Osazones.. . . . . . . . . . . IV. Anhydi ides of Orazones and Hydrazoncs..

3. Action of Rases on Osazones. . . . . . . . . . . . . . . . . . VI. Theories of Osazone Formation.. . . . . . . . . . . . . . . . . . . 23 24 24 26 26 28 28 31 31 33 36 37 37 37 39 40 41 I. INTRODUCTION All carbohydrate chemists will agree that the first notable advance in the subject dates from the publication of the classical papers of Emil Fischer’ on phenylosazone formation. 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.

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