Citation: Xin Zhou, Guangyao Liu, Meifang Yang, Mengyu Li, Xiaodi Yang, Weiliang Gu, Yitian Zhao, Houchao Tao. Glycosyl N-phenyl pentafluorobenzimidates as a new generation of imidate donors for catalytic glycosylation[J]. Chinese Chemical Letters, ;2025, 36(8): 110734. doi: 10.1016/j.cclet.2024.110734 shu

Glycosyl N-phenyl pentafluorobenzimidates as a new generation of imidate donors for catalytic glycosylation

Xin Zhou ^a ,
Guangyao Liu ^b ,
Meifang Yang ^a ,
Mengyu Li ^a ,
Xiaodi Yang ^a ,
Weiliang Gu ^b ,
Yitian Zhao ^{c, *,} ,
Houchao Tao ^{a, *,}

a.
Shanghai Frontiers Science Center of TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
b.
School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
c.
Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, Ningbo 315100, China

zhaoyt@zjpc.net.cn

houchao@shutcm.edu.cn

Received Date: 27 September 2024
Revised Date: 22 November 2024
Accepted Date: 5 December 2024
Available Online: 6 December 2024

Figures(6)

Glycosyl imidates are among the pioneering donors for catalytic glycosylation. We report a new generation of imidates featuring the presence of a pentafluorophenyl group, introduced via substitution on imidoyl fluoride which is easily prepared, stable and user-friendly. The resulting donors exhibit exceptional shelf stability while can be readily activated to achieve high-yielding glycosylation, encompassing comprehensively aldosyl, ketosyl and ulosonyl donors, and both O- and N-glycosylation acceptors. Notably, the reactivity gradient across different generations of imidates, coupled with the accessible imidate acceptor from selective reaction of imidoyl fluoride at the anomeric hydroxyl group, enables a fully catalytic one-pot synthesis of oligosaccharides.
- Catalytic glycosylation,
- Ketosyl and ulosonyl donors,
- One-pot synthesis,
- Imidate,
- Glycosyl donor
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