Abstract
IN attempting to synthesize disaccharides from glucosediethylmereaptal, Brigl, Gronemeier and Schultz (Ber. deutsch. chem. Gesell., May 1939) have obtained an ethyl-thioglucoside with properties very different from those of the α- and β-forms described by Schneider and Sepp (Ber., 1916 and 1918). It is now maintained that the new strongly dextrorotatory compound and the lævo-rotatory so-called β-form both possess the pyranose ring structure, whilst the dextro-rotatory α-form must be a furano-side. Convincing proof of the structure of this furanoside is obtained from experiments with acetone derivatives in which the 5.6 positions must be occupied by the iso-propylidene group. By condensation of glucose diethylmercaptan with acetone in presence of a finely powdered preparation of copper sulphate from which just half the normal water of crystallization had been removed, 5.6-monoiso-propylidene mercaptal was prepared, from which, with the aid of mercuric chloride and cadmium carbonate, 5·6-acetonethioglucoside was formed.
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The Ethyl-Thioglucosides and a New Monoacetoneglucose. Nature 144, 680–681 (1939). https://doi.org/10.1038/144680a0
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DOI: https://doi.org/10.1038/144680a0