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.
- Tandem ene/intramolecular
- Sakurai cyclisation
- Glucose-6-phosphate bioisostere
- NICOTINAMIDE RIBOSIDE
- POLYSUBSTITUTED TETRAHYDROPYRANS
- ANTIVIRAL EVALUATION
- GENETIC SYSTEM