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Issue 15, 2004
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Selective electrochemical glycosylation by reactivity tuning

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Abstract

Electrochemical glycosylation of a selenoglycoside donor proceeds efficiently in an undivided cell in acetonitrile to yield β-glycosides. Measurement of cyclic voltammograms for a selection of seleno-, thio-, and O-glycosides indicates the dependence of oxidation potential on the anomeric substituent allowing the possibility for the rapid construction of oligosaccharides by selective electrochemical activation utilising variable cell potentials in combination with reactivity tuning of the glycosyl donor. A variety of disaccharides are readily synthesised in high yield, but limitations of the use of selenoglycosides as glycosyl donors for selective glycosylation of thioglycoside acceptors are exposed. The first electrochemical trisaccharide synthesis is described.

Graphical abstract: Selective electrochemical glycosylation by reactivity tuning1

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Publication details

The article was received on 23 Dec 2003, accepted on 14 May 2004 and first published on 09 Jul 2004


Article type: Paper
DOI: 10.1039/B316728C
Citation: Org. Biomol. Chem., 2004,2, 2195-2202
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    Selective electrochemical glycosylation by reactivity tuning

    R. R. France, R. G. Compton, B. G. Davis, A. J. Fairbanks, N. V. Rees and J. D. Wadhawan, Org. Biomol. Chem., 2004, 2, 2195
    DOI: 10.1039/B316728C

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