Issue 0, 1973

Chemical modification of trehalose. Part XIII. Synthesis of some 4,4′-difluoro- and 4,4′,6,6′-tetrafluoro-analogues

Abstract

Suitably protected 4,4′-disulphonates and 4,4′,6,6′-tetrasulphonates of trehalose and galacto-trehalose have been subjected to fluoride displacement reactions with tetra-n-butylammonium fluoride in acetonitrile. In the cases of the trehalose sulphonates the reactions proceeded with configurational inversion at C-4 to give the appropriate di- and tetra-fluoro-galacto-trehalose derivatives in moderate yields from which the protecting groups were subsequently removed. On the other hand, the galacto-trehalose sulphonates underwent extensive elimination and in consequence the required di- and tetra-fluorotrehaloses were only obtained in poor yields.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 784-788

Chemical modification of trehalose. Part XIII. Synthesis of some 4,4′-difluoro- and 4,4′,6,6′-tetrafluoro-analogues

L. Hough, A. K. Palmer and A. C. Richardson, J. Chem. Soc., Perkin Trans. 1, 1973, 784 DOI: 10.1039/P19730000784

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