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

• Access to a range of (±) C-glycosides shows the versatility of the tandem ene/IMSC.
• Diastereomerically pure C-glycosides incorporating aromatic moieties were prepared.
• The C-homologue of (±)-β-2-deoxy-glucose 6-phosphate is also reported.

The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the 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 functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate.Figure optionsDownload as PowerPoint slide

The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the 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 functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-β-2-deoxy-glucose 6-phosphate.Figure optionsDownload as PowerPoint slide