Glycosylation with Disarmed Glycosyl Bromides Promoted by Iodonium Ions

Gyrithe Lanz, Robert Madsen

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Abstract

Iodonium ions have been developed for activating glycosyl bromides in the coupling to glycosyl acceptors. The iodonium ions are generated from N-iodosuccinimide and a protic acid such as camphorsulfonic acid or triflic acid, where the latter gives the most reactive promoter system. The couplings occur with the release of iodine monobromide, and the best results are obtained with benzoylated glycosyl donors and acceptors. In this way, disarmed glycosyl bromides can serve as glycosyl donors without the use of heavy-metal salts.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number18
Pages (from-to)3119-3125
Number of pages7
ISSN1434-193X
DOIs
Publication statusPublished - 2016

Keywords

  • Glycosides
  • Glycosyl bromide
  • Halogens
  • Promoters
  • Synthetic methods

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