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AuCl3–tBuCN Catalysis in 1,2-trans 2-Deoxy-2-fluoro Glycosidic Bond Formation

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2025

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Li, Yuanyuan
Zhang, Zhentao
Chen, Xing
Li, Tong
Li, Tianlu

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https://doi.org/10.1021/acs.orglett.5c04361
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National Natural Science Foundation of China: 22177061
National Natural Science Foundation of China: 22577062
National Natural Science Foundation of China: 92478125

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Chemie: Publikationen
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Organic Letters. ACS Publications. 2025, 27(50), S. 13833-13838. ISSN 1523-7060. eISSN 1523-7052. Verfügbar unter: doi: 10.1021/acs.orglett.5c04361

Zusammenfassung

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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540 Chemie

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ISO 690LI, Yuanyuan, Zhentao ZHANG, Xing CHEN, Tong LI, Richard R. SCHMIDT, Peng PENG, Tianlu LI, 2025. AuCl3–tBuCN Catalysis in 1,2-trans 2-Deoxy-2-fluoro Glycosidic Bond Formation. In: Organic Letters. ACS Publications. 2025, 27(50), S. 13833-13838. ISSN 1523-7060. eISSN 1523-7052. Verfügbar unter: doi: 10.1021/acs.orglett.5c04361
BibTex
@article{Li2025-12-08tBuCN-75931,
  title={AuCl<sub>3</sub>–tBuCN Catalysis in 1,2-trans 2-Deoxy-2-fluoro Glycosidic Bond Formation},
  year={2025},
  doi={10.1021/acs.orglett.5c04361},
  number={50},
  volume={27},
  issn={1523-7060},
  journal={Organic Letters},
  pages={13833--13838},
  author={Li, Yuanyuan and Zhang, Zhentao and Chen, Xing and Li, Tong and Schmidt, Richard R. and Peng, Peng and Li, Tianlu}
}
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