Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C−O Bond Homolysis

Yongliang Wei, Benjamin Ben-zvi, Tianning Diao

Research output: Contribution to journalArticlepeer-review


C-aryl glycosyl compounds offer better in vivo stability relative to O- and N-glycoside analogues. C-aryl glycosides are extensively investigated as drug candidates and applied to chemical biology studies. Previously, C-aryl glycosides were derived from lactones, glycals, glycosyl stannanes, and halides, via methods displaying various limitations with respect to the scope, functional-group compatibility, and practicality. Challenges remain in the synthesis of C-aryl nucleosides and 2-deoxysugars from easily accessible carbohydrate precursors. Herein, we report a cross-coupling method to prepare C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from glycosyl esters and bromoarenes. Activation of the carbohydrate substrates leverages dihydropyridine (DHP) as an activating group followed by decarboxylation to generate a glycosyl radical via C−O bond homolysis. This strategy represents a new means to activate alcohols as a cross-coupling partner. The convenient preparation of glycosyl esters and their stability exemplifies the potential of this method in medicinal chemistry.

Original languageEnglish (US)
Pages (from-to)9433-9438
Number of pages6
JournalAngewandte Chemie - International Edition
Issue number17
StatePublished - Apr 19 2021


  • C-glycosylation
  • cross-coupling
  • glycosyl radicals
  • nucleoside analogues
  • photoredox

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry


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