Chemistry

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.)

ISBN-10: 0120072033

ISBN-13: 9780120072033

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A similar result was obtained with Dgalactose phenylosazone22from which on complete methylation a crystalline trimethyl-D-galactose methylphenylphenylosazone was obtained, no more methoxy groups entering the molecule. Accordingly D-galactose phenylosazone has been designated as D-tagatopyranose phenylosazone. Contrary views have been expressed by Enge123who also carried out methylation experiments with D-glucose phenylosazone. 0% should have been obtained. This result therefore is not in conflict with the cyclic structure.

28, 1145 (1895). (20) The Fischer-Rosanoff system has been occasionally referred to as the WohlFreudenberg system through lack of regard for the clear historical record. A. Wohl and K. , 66,309 (1923)]adopted the Fiacher-Rosanoff system years after i t had been followed by many other chemists in numerous publications. EMIL FISCHER'S STEREO-FORMULAS 17 The experimental facts from which the writer inferred" his isorotation rules indicated that the arrangements of the groups that are attached to carbon atom 1in the a- and p-forms of sugars and glycosides of supposedly one and the same type of ring structure, as was then assumed, could be brought into a correlated configurational system through a knowledge of the relative values of the rotations of the substances.

250) P. Karrer and K. Pfaehler, Helv. Chim. A d a , 17, 766 (1934). E. Chargaff and B. Magassnik, J. Am. Chem. , 69, 1459 (1947). 31 HYDRAZONE AND OSAZONE DERIVATIVES OF SUQARB such as exists, for example, in solutions of D-glucopyranose, which is also completely disrupted by periodic acid. The stability of the pyranose ring in XI1 must be compared, therefore, with the pyranose ring in a reducing sugar rather than in a glycoside, which would explain the apparently conflicting results discussed above.

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


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