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C-Glycosides are metabolically stable mimics of natural O-glycosides and are expected to be useful tools for investigation of the biological functions of glycans. Here, we describe the synthesis of a… Click to show full abstract
C-Glycosides are metabolically stable mimics of natural O-glycosides and are expected to be useful tools for investigation of the biological functions of glycans. Here, we describe the synthesis of a series of aryl and vinyl C-glycosides by stereoinvertive sp3-sp2 cross-coupling reactions of 2-deoxyglycosyl boronic acid derivatives with aryl or vinyl halide, mediated by a photoredox/nickel dual catalytic system. Hydrogenation of the vinyl C-glycosides afforded C-linked 2'-deoxydisaccharide analogues.
Keywords:
glycosylation synthesis;
trifluoroborates precursors;
direct glycosylation;
precursors direct;
glycosyl trifluoroborates;
synthesis
Journal Title: Organic letters
Year Published: 2021
Link to full text (if available)
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Journal Title: Organic letters
Year Published: 2021
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!