Selective electrochemical glycosylation by reactivity tuning

Robert R. France; Richard G. Compton; Benjamin G. Davis; Antony J. Fairbanks; Neil V. Rees; Jay D. Wadhawan

doi:10.1039/B316728C

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Selective electrochemical glycosylation by reactivity tuning¹

Robert R. France,^a Richard G. Compton,*^b Benjamin G. Davis,^a Antony J. Fairbanks,*^a Neil V. Rees^b and Jay D. Wadhawan^b

Author affiliations

* Corresponding authors

^a Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford, UK
E-mail: antony.fairbanks@chem.ox.ac.uk

^b Physical and Theoretical Chemistry Laboratory, South Parks Road, Oxford, UK

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.

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Article information

DOI: https://doi.org/10.1039/B316728C
Article type: Paper
Submitted: 23 Dec 2003
Accepted: 14 May 2004
First published: 09 Jul 2004

Download 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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Organic & Biomolecular Chemistry