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

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

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SJQ,6-Trirnethy~-~-Galactose Levene and Meyer,lo by methylation of 1,2-isopropylidene-~-galactopyranose, obtained a sirupy trimethyl-D-galactose which was apparently the 3,4,6-derivative. The reasons for assigning the above quoted structure were fairly obvious: (a) The monoacetone compound, obtained from diacetone galactose, which has a free hydroxyl group in position 6, is non-reducing; (b) the lactone obtained by HOBr oxidation of the free sugar displays a rotation change characteristics of the b-lactones of aldonic acids.

Z. Hassid, M. Doudoroff and H. A. Barker, J . Am. Chem. , 66, 1416 (1944). THE SYNTHESIS OF OLIGOSACCHARIDES 35 the structure of sucrose, but it does indicate how sucrose might be synthesized in nature. Of the common sugars, only those containing the sucrose and the maltose type linkages still challenge the carbohydrate chemist to obtain them by a true chemical synthesis. Some of the difficulties have been indicated for the synthesis of the sucrose linkage, which is also present in raffinose and gentianose.

N. Haworth, J. V. Loach and C. W. Long, J . Chem. ,3146 (1927). (45) J. K. N. Jones and F. , 4, 243-291 (1949). (46) W. N. Haworth, E. L. Hirst and J. A. B. Smith, J . Chem. , 2659 (1930). 6 +go. 2 51 (21 hrs. Schlubach and K. , 66, 1957 (1923). (48) J. C. Irvine and D. McNicoll, J . Chem. , 97, 1449 (1910). (49) E. Baldwin and D. J. Bell, J . Chem. ,1461 (1938). (50) D. J. Bell, J . Chem. , 1543 (1940). D. Drew, E. H. Goodyear and W. N. Hrtworth, J . Chem. , 1237 (1929). (52) J. Pryde, E. L. Hirst and R.

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