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AuCl3-tBuCN Catalysis in 1,2-trans 2-Deoxy-2-fluoro Glycosidic Bond Formation
Yuanyuan Li1,2,3, Zhentao Zhang1,2, Xing Chen1,2
1Shenzhen Research Institute of Shandong University, A301 Virtual University Park in South District of Shenzhen, Shenzhen, Guangdong 518057, China.
Abstract:
Herein we report a general and efficient AuCl3-tBuCN cooperative catalysis system for the synthesis of 1,2-trans 2-deoxy-2-fluoro-glycosides. The reaction proceeds rapidly (15 min) under mild conditions, affording high stereoselectivity across a broad range of glycosyl donors and acceptors (40 examples, up to quantitative yield), thus enabling the streamlined chemoenzymatic assembly of fluorinated analogues of human milk oligosaccharides (HMOs). The current work provides a practical solution to long-standing challenges in the stereoselective construction of fluorinated carbohydrates.
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