Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties

Philip Redpath, Kerry A. Ness, Joanne Rousseau, Simon J. F. Macdonald, Marie E. Migaud*

*Corresponding author for this work

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to thesynthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation ofthe glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series,we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalisedaromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of(±)-b-2-deoxy-glucose 6-phosphate.
Original languageEnglish
Pages (from-to)25-34
Number of pages10
JournalCarbohydrate Research
Volume402
Early online date11 Nov 2014
DOIs
Publication statusPublished - 30 Jan 2015

Keywords

  • Tandem ene/intramolecular
  • Sakurai cyclisation
  • Transmetallation
  • C-Nucleoside
  • C-Glycoside
  • Glucose-6-phosphate bioisostere
  • NICOTINAMIDE RIBOSIDE
  • POLYSUBSTITUTED TETRAHYDROPYRANS
  • ANTIVIRAL EVALUATION
  • GENETIC SYSTEM
  • NUCLEOSIDES
  • ANALOGS
  • NAD(+)
  • CHEMISTRY
  • ROUTE
  • BASES

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