CX.—The alkylation of galactose
James Colquhoun Irvine, Adam Cameron
1904
Journal of the Chemical Society Transactions
A METHOD of obtaining alkylated derivatives of sugars in which the hydroxyl groups of the parent substance are partially or completely replaced by methoxyl has been described in a recent paper (Trans., 1903(Trans., , 83, 1021. The process consists in alkylating a soluble glucoside by means of dry silver oxide and methyl iodide, the final product of this reaction being a completely methylated sugar of glucosidic structure. These compounds on hydrolysis lose only the glucosidic alkyl group, and
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... eld an alkylated aldose or ketose possessing most of the properties of a reducing sugar. Although the method mems to be a general one, the only compounds of this class which so far have been studied in detail are the various dkylated derivatives of glucose. The present paper deals with the preparation and examination of the isomeric tetramethyl a-and /3-methylgalactosides and with the alkylated sugar obtained from these compounds by hydrolysis. The material used as a starting point was Fiacher's u-methylgalactoside, which was purified as far as possible from the p-form by recrystallisation from ethyl acetate. Alkylation by means of dry silver oxide and methyl iodide was effected in the first place in methylalcoholic solution, and finally, when the met hylation had proceeded far enough, in methyl iodide. The product of this reaction was tetramethyl a-methylgalsctoside, which boiled a t 136-137' under 11 mm. pressure. Like the corresponding alkylated glucoside, this compound is a colourless, refrdctive liquid, readily soluble in organic solvents. In the pure state, the compound showed a specific rotation of + 105.7O, and this agrees approximately with the value given by a 10 per cent. solution in alcohol, which equals + 109.9'.
doi:10.1039/ct9048501071
fatcat:qhq75u3hb5fxfc5awk5aaunkjy