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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S. Hudson, J . Am. Chem. ,31, 66 (1909). Fischer, “Untersuchungen,” p. 88. 16 C. 5. HUDSON enantiomorphs of this pair of glucosides, and heI8named them “ a-methylZ-glucoside” (- 159’) and “p-methyl-Z-glucoside ” (+34’). The attention of the reader is especially directed to these names. I t should be carefully noted that the two members of each pair of enantiomorphs bear customary opposite symbols (corresponding to the present D and L) for the parent sugar but one symbol only (afor one pair, p f o r the other) in designation of the asymmetric arrangement o n carbon atom 1.

Muir and E. G. V. Percival, J . Chem. ,1479 (1940). (23) L. L. Engel, J . Am. Chem. , 67,2419 (1935). 30 E. 0. V. PERCIVAL He shows t ha t D-fructose methylphenylosazone in contact with phenylhydrazine at room temperature yields D-fructose methylphenylphenylosazone and with p-nitrophenylhydrazine, D-fructose methylphenyl-pnitrophenylosazone. It is possible to interpret this result in another way, namely t hat since the competing base removes one methylphenylhydrazine residue but not both, one is less firmly bound than the other, and might be admitted as evidence that the two methylphenylhydrazine residues are bound by different types of linkage t o the sugar, as in fact the cyclic formulation demands.

When Haworth22and his coworkers discovered that the tetramethy1-Dglucose which results from the acid hydrolysis of either the a- or 0-anomer of fully methylated normal methyl glucoside is a 2,3,4,64etramethyl-~glucose, it became apparent that the oxygen bridge connects carbon atoms 1 and 5. In the abnormal or ‘‘ y ” type of glucoside this bridge was found to connect carbon atoms 1 and 4. Similar structures were disclosed in the fructose series, where the bridges were between carbon atoms 2 and 6 in the normal forms and between 2 and 5 in those of the “ y l l type.

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