By Claude S. Hudso (ed.), Sidney M. Canto (ed.)
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Additional info for Advances in Carbohydrate Chemistry, Vol. 6
Chem. , 1543 (1940). D. Drew, E. H. Goodyear and W. N. Hrtworth, J . Chem. , 1237 (1929). (52) J. Pryde, E. L. Hirst and R. W. Humphreys, J . Chem. , 127, 348 (1925). This Page Intentionally Left Blank THE SYNTHESIS OF OLIGOSACCHARIDES BY W. L. EVANS, D. D. REYNOLDSAND E. A. TALLEY The Ohio State University, Eastman Kodak Company, Eastern Regional Research Columbus, Ohio Rochester, New York Laboratory, U. S. Department of Agriculture, Philadelphia, Pennsylvanaa CONTENTS I. Introduction . . . .
Formation of the OligosaccharideLmkage. . . . . . . . . . . . . a. Enzymatic Syntheses . . . . . . . . . . . . . . . . . . . b. Action of Dehydrating Agents.. . . . . . . . . . . . . . . c. Koenigs-Knorr Reaction. . . . . . . . ............... d. Addition to Compounds of Ethylene Oxide e . . . . . . . e. Alkali Salt Elimination.. 2. Alteration of the Oligosaccharide Linkage. . . . 31 35 36 39 41 50 51 a. The Lobry de Bruyn and van Ekenstein Rearrangement c.
29) (30) (31) (32) E. T. Dewar and E. G. V. Percival, J . Chem. ,1622 (1947). D. J. Bell, J . Chem. ,692 (1945). D. J. Bell, J . Chem. ,992 (1948). J. S. D. Bacon and D. J. Bell, J . Chem. ,1869 (1939). THE METHYL- ETHERS OF D-GALACTOSE 19 5 . 4,6-Dimethyl-~Galactose The synthesis of this sugar presented certain technical problems. While the obvious starting material was either of the methyl 4,6-benzylidene-pgalactopyranosides it was quite clear that neither carboxylic nor sulphonic nor nitric esters could be used for temporary masking of hydroxyls 2 and 3.
Advances in Carbohydrate Chemistry, Vol. 6 by Claude S. Hudso (ed.), Sidney M. Canto (ed.)