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

Fingerprint

Scaffolds
Galactosides
Glucose-6-Phosphate
Cyclization
Glucosides
Derivatives
C-glycoside

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

Cite this

Redpath, Philip ; Ness, Kerry A. ; Rousseau, Joanne ; Macdonald, Simon J. F. ; Migaud, Marie E. / Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties. In: Carbohydrate Research. 2015 ; Vol. 402. pp. 25-34.
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Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties. / Redpath, Philip; Ness, Kerry A.; Rousseau, Joanne; Macdonald, Simon J. F.; Migaud, Marie E.

In: Carbohydrate Research, Vol. 402, 30.01.2015, p. 25-34.

Research output: Contribution to journalArticle

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AU - Ness, Kerry A.

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KW - NUCLEOSIDES

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KW - NAD(+)

KW - CHEMISTRY

KW - ROUTE

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