Selective electrochemical glycosylation by reactivity tuning

Research output: Contribution to journalArticle

Authors

  • R.R. France
  • B.G. Davis
  • A.J. Fairbanks
  • R.G. Compton
  • J.D. Wadhawan

Colleges, School and Institutes

External organisations

  • OXFORD UNIVERSITY
  • Phys./Theor. Chemistry Laboratory

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.

Details

Original languageEnglish
Pages (from-to)2195-2202
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number15
Publication statusPublished - 7 Aug 2004