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Recent development in the synthesis of <i>C</i>-glycosides involving glycosyl radicals

Lin-Yi Xu, Nai-Li Fan, Xiang‐Guo Hu

2020Organic & Biomolecular Chemistry199 citationsDOI

Abstract

C-Glycosylation involving glycosyl radical intermediates is a particularly effective approach to access C-glycosides, which are core units of a great number of natural products, bioactive compounds and marketed drugs. In this review, we summarize the progress of glycosyl radical-based C-glycoside synthesis between 1999-2020, focusing on the stereoselectivity and recently developed methodologies such as α-alkoxyacyl telluride-related, photo-mediated and transition-metal catalysed reactions. Metal-mediated reductive cross coupling is also covered due to its close relationship with the latter approaches. To introduce several strategies for achieving uncommon β-stereoselective C-glycosylation, we also briefly described organotin-based methods.

Topics & Concepts

GlycosylStereoselectivityGlycosylationRadicalChemistryGlycosideCombinatorial chemistryGlycosyl donorStereochemistryOrganic chemistryCatalysisBiochemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsOxidative Organic Chemistry Reactions
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