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Updated: Aug 26, 2025

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Recent development of stereoselective C-glycosylation via generation of glycosyl radical
1Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-Minami, 680-8552, Tottori, Japan.
Abstract:
C-glycosylation through the formation of glycosyl radical is a very feasible and expedient approach for making of the C-C anomeric bond. In this light, this review article is covering selected literature from 2000 to 2022 on the synthetic development of C-glycosylation involving the generation of glycosyl radical as a crucial intermediate in a stereoselective fashion. The generation of glycosyl radical is controlled by the reaction method applying to the radical precursor. Those methods are categorized in terms of a key source of an initiator such as metal-free activation of radical precursor, photochemical induced approach, and metal-mediated approach including transition metal-mediated, lanthanide, and non-transition metal-mediated approach with brief mechanistic discussion, and stereochemical outcome of resultant C-glycosides in detail. This brief discussion accumulates the stereoselective synthesis of challenging C-linked building blocks in a more facile way via generation of glycosyl radical and those building blocks have a great role as drugs, inhibitors, glycoconjugates in the field of biological and medicinal chemistry.
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