Citation: Shuai Liu, Le Liu, De-Yong Liu, Nai-Li Fan, Xiang-Guo Hu. Generation of glycosyl radicals from phosphitylated 1-hydroxycarbohydrates for the deoxygenative synthesis of C-alkyl glycosides[J]. Chinese Chemical Letters, ;2026, 37(12): 112505. doi: 10.1016/j.cclet.2026.112505 shu

Generation of glycosyl radicals from phosphitylated 1-hydroxycarbohydrates for the deoxygenative synthesis of C-alkyl glycosides

National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China

shuailiu@jxnu.edu.cn

xiangguo.hu@jxnu.edu.cn

Received Date: 27 November 2025
Revised Date: 30 January 2026
Accepted Date: 5 February 2026
Available Online: 7 February 2026

Figures(5)

We have established a glycosyl radical-based synthesis of C-alkyl glycosides, utilizing a deoxygenative Giese reaction between alkenes and phosphitylated 1-hydroxycarbohydrates. This approach introduces a novel strategy to generate glycosyl radicals through SET reduction enabled by 2–iodophenethyl methyl phosphite. It operates under mild conditions, avoids the use of toxic hydrogen-atom donors while utilizing readily available precursors. The protocol is also amenable to late-stage functionalization of drug molecules and scale-up using continuous-flow. Mechanistic studies confirm the formation of glycosyl radicals and indicate that the hydrogen atoms originate from TMS₃SiH.
- Glycosyl radical,
- C-Glycosides,
- Giese-type addition,
- Hydroglycosylation,
- Radical deoxygenation
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