Recent development in the synthesis of -glycosides involving glycosyl radicals

• Published in: Organic & biomolecular chemistry 2020-07, Vol.18 (27), p.595-519
• Main Authors: Xu, Lin-Yi, Fan, Nai-Li, Hu, Xiang-Guo
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d0ob00711k

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. 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.