Advances in Carbohydrate Chemistry, Vol. 6 by Claude S. Hudso (ed.), Sidney M. Canto (ed.)

By Claude S. Hudso (ed.), Sidney M. Canto (ed.)

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It has not yet been synthesized. On the basis of calculations of rotations by HudsonJ4' the isotrehalose of Fischer and Delbruck was p,p-trehalose, in impure form. (46) H. A. L. , 1, 173 (1832). (47) C. 8. Hudson, J . Am. Chem. , 88, 1571 (1916). 40 W. L. EVANS, D. D. REYNOLDS AND E. A. TALLEY A number of years later, Schlubach and Maurer4*tried a number of modifications with the idea that an acid catalyst might cause the alpha configuration to predominate and give them the natural trehalose, since alkaline catalysts seemed to give the beta derivatives.

Doudoroff, Advances in Enzymology, 10, 123 (1950). (43) W. 2. Hassid, M. Doudoroff, A. L. Potter and H. A. Barker, J . Am. Chem. , 70, 306 (1948). (44) H. Wolochow, E. W. Putnam, M. Doudoroff, W. 2. Hassid and H. A. Barker, J . Biol. , 180, 1237 (1949). (45) W. 2. Hassid, Paper presented before the Division of Sugar Chemistry and Technology, Am. Chem. , April (1950). 39 THE SYNTHESIS OF OLIQOSACCHARIDES Syntheses using enzymes as catalysts give rather low yields. The main value of the method lies in its similarity to the processes probably occurring in nature.

60 Conclusion.. . . . . . . . . . . . . . . . . . . . . . . . . . . . Table of Glycosyl Halides.. . Table of Compounds of Alcoholic Type. . . . . . . . . . . . . . . . Table of Oligosaccharides.. . . . . . . . . . . . . . . . . . . . . . 65 g. The Wohl-ZemplBn Degradation IV. V. VI. VII. . . . . . . . 58 . . . . . . . 59 67 70 I. INTRODUCTION The synthesis of oligosaccharides has played an important part in the development of carbohydrate chemistry.

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