C-Glycosides,known for their superior in vivo stability compared to their O-and N-glycoside counterparts,have been widely explored as drug candidates and utilized in biological research.Traditional radical C-glycosida...C-Glycosides,known for their superior in vivo stability compared to their O-and N-glycoside counterparts,have been widely explored as drug candidates and utilized in biological research.Traditional radical C-glycosidation techniques relied on precursors such as glycosyl halides and glycosyl sulfones.These methods,however,face several challenges,including the instability of glycosyl precursors,the requirement for multi-step synthesis,and limited practicality.Herein,we present a straightforward,metal-free method to synthesize both sp^(2) and sp^(3) Cglycosides with high stereoselectivity via direct deoxy-glycosidation of readily available and stable 1-hydroxycarbohydrates.Mechanistic investigations indicate the involvement of glycosyl radicals in the reaction.Cellular assays reveal the antitumor activity of the synthesized products,which underscores the potential of this strategy in medicinal chemistry.展开更多
基金supported by the National Key R&D Program of China(No.2022YFA1505100 and 2021YFA1500100)National Natural Science Foundation of China(Nos.22031008,A.L.+1 种基金212200007,W.L.)the Science Foundation of Wuhan(No.2020010601012192).
文摘C-Glycosides,known for their superior in vivo stability compared to their O-and N-glycoside counterparts,have been widely explored as drug candidates and utilized in biological research.Traditional radical C-glycosidation techniques relied on precursors such as glycosyl halides and glycosyl sulfones.These methods,however,face several challenges,including the instability of glycosyl precursors,the requirement for multi-step synthesis,and limited practicality.Herein,we present a straightforward,metal-free method to synthesize both sp^(2) and sp^(3) Cglycosides with high stereoselectivity via direct deoxy-glycosidation of readily available and stable 1-hydroxycarbohydrates.Mechanistic investigations indicate the involvement of glycosyl radicals in the reaction.Cellular assays reveal the antitumor activity of the synthesized products,which underscores the potential of this strategy in medicinal chemistry.
