Citation: Yidian Mo, Ao Sun, Hang Dong, Zhongtang Li, Zhongjun Li. Synthesis of α-d-fructofuranosides and difructose dianhydride Ⅳ using glycosyl fluorides as donors[J]. Chinese Chemical Letters, ;2026, 37(7): 111922. doi: 10.1016/j.cclet.2025.111922 shu

Synthesis of α-d-fructofuranosides and difructose dianhydride Ⅳ using glycosyl fluorides as donors

Yidian Mo ^{a, b} ,
Ao Sun ^b ,
Hang Dong ^b ,
Zhongtang Li ^{a, b, *,} ,
Zhongjun Li ^{a, b, *,}

a.
Ningbo Institute of Marine Medicine, Peking University, Ningbo 315832, China
b.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China

lizhongtang@bjmu.edu.cn

zjli@bjmu.edu.cn

Received Date: 30 July 2025
Revised Date: 11 September 2025
Accepted Date: 29 September 2025
Available Online: 4 October 2025

Figures(6)

α-d-Fructofuranoside derivatives are prevalent in natural products, exhibiting diverse bioactivities. Herein, a stereoselective glycosylation method for synthesizing α-d-fructofuranosides using fructofuranosyl fluorides as donors is described. Glycosylation of 1,3,4,6-tetra-O-benzoyl-2-d-fructofuranosyl fluoride, promoted by tris(pentafluorophenyl)borane, proved highly effective, yielding glycosylation products in high yields (up to 98%) with primary alcohols, thiols, N- and C-nucleophiles. Furthermore, β-(2→6) cyclodisaccharide di-d-fructose-2,6′:6,2′-dianhydride (DFA Ⅳ), a disaccharide enzymatically derived from levan, was chemically synthesized through orthogonal glycosylation reactions and hydrogen-bond-mediated aglycone delivery involving thioglycosides and glycosyl fluorides for the first time.
- Glycosylation,
- Fructofuranosides,
- Stereoselectivity,
- Glycoderivatives,
- DFA Ⅳ
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