Advances in Carbohydrate Chemistry, Vol. 6 - download pdf or read online

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

ISBN-10: 0120072068

ISBN-13: 9780120072064

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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. The Aluminum Chloride Rearr d. The Hydrogen Fluoride Rearr e.

3~ The constitution assigned to the sugar followed from the following arguments : ( a ) Treatment with phenylhydrazine yielded a dimethyl galactosazone identical with that derived from 2,4,6-trimethylD-galactose ( q . v . ) ; ( b ) the ditosylated glycoside did not react with sodium iodide in acetone; (c) the sugar, in presence of methanolic hydrogen chloride, showed polarimetric behavior characteristic of a sugar substituted in position 4. 6. Characterization of Dimethyl-D-Galactoses As an aid to workers who may have need to identify a dimethylgalactose there are recorded in Table I1 appropriate data and references.

Stacey, J . Chem. I ~ O C . , 622 (1946). + B-D-Galactopyranose = Lactose + 30 W. L. EVANS, D. D. REYNOLDS AND E. A. TALLEY HC=O HC=O HC=O HC=O HbOH HboH HAoH HboH H d H +iiidH HobH ,:/HAOH , ' = HoAH AH +HIO 8 /&OH HAOH;: HAOH HAOH I H 2 b :6xi H J O H HzA HiCOH HAOH D-Galactose + D-Glucose = 6-~-Galnctose3-~-glucoseether + Water HO H ~ P Third Type this chapter wherever the ring structure is unknown or is not stabilized. Otherwise the Haworth type formulas will be used. In actual practice, as will be apparent later, the formation of these linkages is not as simple as is implied by the equations given above.

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


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