A modular and general method to make unprotected aryl C-glycosides with high stereoselectivity from simple starting materials has been developed based on photoredox, Ni-catalysed cross-coupling. Key to success is the use of an allyl glycosyl sulfone in combination with tolyl sulfinate as the synthetic equivalent of a glycosyl anion.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 digital issues and online access to articles
$119.00 per year
only $9.92 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
References
Yang, Y. & Yu, B. Recent advances in the chemical synthesis of C-glycosides. Chem. Rev. 117, 12281–12356 (2017). A review article that summarizes advances in aryl C-glycoside synthesis.
Gong, H. & Gagné, M. R. Diastereoselective Ni-catalyzed Negishi cross-coupling approach to saturated, fully oxygenated C-alkyl and C-aryl glycosides. J. Am. Chem. Soc. 130, 12177–12183 (2008). This paper represents an early example of preparing aryl C-glycosides from glycosyl radicals by Ni catalysis.
Wan, L.-Q. et al. Nonenzymatic stereoselective S-glycosylation of polypeptides and proteins. J. Am. Chem. Soc. 143, 11919–11926 (2021). This paper reports the debut of allyl glycosyl sulfones as glycosyl donors.
Zhang, C. et al. Halogen-bond-assisted radical activation of glycosyl donors enables mild and stereoconvergent 1,2-cis-glycosylation. Nat. Chem. 14, 686–694 (2022). This paper reports the use of allyl glycosyl sulfones in O-glycoside synthesis.
Yi, L., Ji, T., Chen, K.-Q., Chen, X.-Y. & Rueping, M. Nickel-catalyzed reductive cross-couplings: new opportunities for carbon–carbon bond formations through photochemistry and electrochemistry. CCS Chem. 4, 9–30 (2022). A review article that summarizes photoredox Ni-catalysed cross-coupling reactions.
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
This is a summary of: Zhang, C. et al. Direct synthesis of unprotected aryl C-glycosides by photoredox Ni-catalysed cross-coupling. Nat. Synth. https://doi.org/10.1038/s44160-022-00214-1 (2023).
Rights and permissions
About this article
Cite this article
Simplifying the synthesis of aryl C-glycosides. Nat. Synth 2, 207–208 (2023). https://doi.org/10.1038/s44160-022-00215-0
Published:
Issue Date:
DOI: https://doi.org/10.1038/s44160-022-00215-0