Stereoselective assembly of C-oligosaccharides via modular difunctionalization of glycals

Ya-Nan Ding, Mei-Ze Xu, Yan-Chong Huang, Lutz Ackermann (), Xiangtao Kong (), Xue-Yuan Liu () and Yong-Min Liang ()
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Ya-Nan Ding: Lanzhou University
Mei-Ze Xu: Lanzhou University
Yan-Chong Huang: Lanzhou University
Lutz Ackermann: Georg-August-Universität
Xiangtao Kong: Anyang Normal University
Xue-Yuan Liu: Lanzhou University
Yong-Min Liang: Lanzhou University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract C-oligosaccharides are found in natural products and drug molecules. Despite the considerable progress made during the last decades, modular and stereoselective synthesis of C-oligosaccharides continues to be challenging and underdeveloped compared to the synthesis technology of O-oligosaccharides. Herein, we design a distinct strategy for the stereoselective and efficient synthesis of C-oligosaccharides via palladium-catalyzed nondirected C1–H glycosylation/C2-alkenylation, cyanation, and alkynylation of 2-iodoglycals with glycosyl chloride donors while realizing the difunctionalization of 2-iodoglycals. The catalysis approach tolerates various functional groups, including derivatives of marketed drugs and natural products. Notably, the obtained C-oligosaccharides can be further transformed into various C-glycosides while fully conserving the stereochemistry. The results of density functional theory (DFT) calculations support oxidative addition mechanism of alkenyl-norbornyl-palladacycle (ANP) intermediate with α-mannofuranose chloride and the high stereoselectivity of glycosylation is due to steric hindrance.

Date: 2024
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DOI: 10.1038/s41467-024-47060-7

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