Abstract
ALTHOUGH it is now well established1,2,3 that the alkaline hydrolysis of suitably substituted hexoses carrying sulphate groups on either the 3 or 6 positions readily yields 3 : 6 anhydrohexose derivatives, all our attempts to obtain evidence for the formation of ethylene oxide rings have been, until recently, unsuccessful, in marked contrast to the behaviour of the toluene-p-sulphonates4. It is now evident that this has been due largely to the fact that the barium salts of the sugar ethereal sulphates investigated were insoluble in organic solvents and the hydrolyses had, in consequence, to be carried out in aqueous media. Under such conditions experimental difficulties arise, for any ethylene oxide derivatives which may have been formed would be hydrolysed with accompanying Walden inversions4. Thus since the ethylene oxide ring formation would also involve a Walden inversion on the carbon atom where the sulphate group was originally attached, the production in recognizable quantity of a derivative of a hexose different from that in the original starting material depends on the relative ease of fission of the two ethylene oxide ring linkages. Thus the hydrolysis of a derivative of glucofuranose-3-sulphate could yield a 2 : 3 anhydro-allofuranose, which might give either a gluco- or an altrofuranose derivative, or both3.
Similar content being viewed by others
Article PDF
References
Percival and Soutar, J. Chem Soc., 1475 (1940).
Duff and Percival, J. Chem. Soc., 830 (1941).
Percival, J. Chem. Soc., 119 (1945).
Peat, Ann. Rep. Chem. Soc., 260 (1939).
Bell, J. Chem. Soc., 1553 (1936).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
PERCIVAL, E., DUFF, R. Production of a Derivative of 5 : 6 Anhydroglucose by the Hydrolysis of an Ethereal Sulphate. Nature 158, 29 (1946). https://doi.org/10.1038/158029a0
Issue Date:
DOI: https://doi.org/10.1038/158029a0
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.