Stereoselective gold(I)-catalyzed approach to the synthesis of complex α-glycosyl phosphosaccharides

Xiaojuan Zhang, Yutong Yang, Jiahao Ding, Yun Zhao, Hongbin Zhang and Yugen Zhu ()
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Xiaojuan Zhang: Yunnan University
Yutong Yang: Yunnan University
Jiahao Ding: Yunnan University
Yun Zhao: Yunnan University
Hongbin Zhang: Yunnan University
Yugen Zhu: Yunnan University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract Glycosyl phosphosaccharides represent a large and important family of complex glycans. Due to the distinct nature of these complex molecules, efficient approaches to access glycosyl phosphosaccharides are still in great demand. Here, we disclose a highly efficient and stereoselective approach to the synthesis of biologically important and complex α-glycosyl phosphosaccharides, employing direct gold(I)-catalyzed glycosylation of the weakly nucleophilic phosphoric acid acceptors. In this work, the broad substrate scope is demonstrated with more than 45 examples, including glucose, xylose, glucuronate, galactose, mannose, rhamnose, fucose, 2-N3-2-deoxymannose, 2-N3-2-deoxyglucose, 2-N3-2-deoxygalactose and unnatural carbohydrates. Here, we show the glycosyl phosphotriester prepared herein was successfully applied to the one-pot synthesis of a phosphosaccharide from Leishmania donovani, and an effective preparation of a trisaccharide diphosphate of phosphosaccharide fragments from Hansenula capsulate via iterative elongation strategy is realized.

Date: 2022
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DOI: 10.1038/s41467-022-28025-0

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