[R 4N] [AOT]: A surfactant ionic liquid as a mild glycosylation promoter

M. Carmen Galan*, Anh Tuan Tran, Julien Boisson, David Benito, Craig Butts, Julian Eastoe, Paul Brown

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)

Abstract

[RN 4][AOT] is a versatile surfactant ionic liquid that can be used in combination with N-Iodosuccinimide to promote the room temperature glycosylation of thiophenyl glycoside donors. The conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range of donors and protecting groups. Under these conditions, a different range of disaccharides have been obtained in good to excellent yields and good stereoselectivities. Furthermore, the anomeric outcome of the glycosylation reaction using glycosyl donors with no participating group at C-2 could be tuned by switching the solvent from DCM to MeCN. © 2011 Copyright Taylor and Francis Group, LLC.

Original languageEnglish
Pages (from-to)486-497
Number of pages12
JournalJournal of Carbohydrate Chemistry
Volume30
Issue number7-9
DOIs
Publication statusPublished - 1 Sep 2011

Keywords

  • Glycosylation
  • Ionic liquids
  • Oligosaccharides
  • Surfactant ionic liquids

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