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

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

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J. Org. , 4, 410 (1939). (11) R. , 26, 1165 (1905). (12) Elizabeth E. Percival and E. G . V. Percival, J . Chem. , 1320 (1937). (13) W. J. Heddlc and E. G . V. Percival, J . Chem. , 1511 (1940). (14) Elizabeth E. Percival and E. G. V. Pcrcival, J . Chem. , 750 (1941). (15) hl. L. Wolfrom and C. C. Christman, J . Am. Chem. , 65, 3413 (1931). HYDRAZONE AND OSAZONE D E R N A T N E S O F SUGARS 27 and Wolfromls who showed that D-galactose 2,3,4,6-tetraacetate (VII) and D-galactose 2,3,5,6-tetraaeetate (VIII) could be converted into the corresponding phenylhydrazones and also into the methylphenylhydrazones IX and X, respectively.

The enantiomorphous phenylosazones from mannose and some salts of mannonic acid behave in the samc way and unquestionably such reversals will be observed frequently as researches in the sugar group are extended. If various compounds which belong exclusively in one series are designated by the prefixes dextro- and levo-rotatory, mistakes through interchange will be unavoidable. Therefore I suggest t h at all compounds of such a series be designated according to the direction of rotation of the aldehyde (sugar) either with the letter d (deslro) or I (levo) or dl (inactive), just as the letters o, m and p are used in th e case of benzene derivatives, At this far later time, it is readily apparent that although this proposal of Fischer’s served his immediate need of describing the enantiomorphs in the mannose series, it would soon prove faulty in respect to that part of the definition which implied that each aldose was to be named d or 1 from its sign of rotation.

Convereion of Osazoncs into Osotriazoles. . . . . . . . . . . . . 2. Hydrogenation of Osazones. . . . . . . . . . . . . . . . . . 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.

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