Citation: Yulu Zhan, Yingshuang Hui, Shuqi Wang, Lou Gao, Yangbin Shen, Zhen-Hua Li, Yahong Zhang, Yi Tang. One-step selective dehydrogenation of cyclic hemiacetal sugars toward to their chiral lactones[J]. Chinese Chemical Letters, ;2023, 34(4): 107677. doi: 10.1016/j.cclet.2022.07.020 shu

One-step selective dehydrogenation of cyclic hemiacetal sugars toward to their chiral lactones

Yulu Zhan ^a ,
Yingshuang Hui ^a ,
Shuqi Wang ^a ,
Lou Gao ^a ,
Yangbin Shen ^b ,
Zhen-Hua Li ^{a, *,} ,
Yahong Zhang ^{a, *,} ,
Yi Tang ^a

a.
Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Laboratory of Advanced Materials, Collaborative Innovation Centre of Chemistry for Energy Materials, Fudan University, Shanghai 200433, China
b.
Institute of Materials Science and Devices, Suzhou University of Science and Technology, Suzhou 215009, China

lizhenhua@fudan.edu.cn

zhangyh@fudan.edu.cn

Received Date: 13 May 2022
Revised Date: 2 July 2022
Accepted Date: 12 July 2022
Available Online: 17 July 2022

Figures(3)

Chiral glycosyl lactone is an important class of bioactive compound and pharmaceutical intermediate in nature, especially for chiral lactones with 4 carbon atoms, which are very useful building blocks for synthesis of biologically interesting compounds. Herein, a selective dehydrogenation and solvent matched catalytic system under oxygen-free conditions was developed to try to achieve the one-step direct conversion of cyclic hemiacetal sugars toward their chiral glycosyl lactones. During the process, the inherent structural characteristics of sugar was efficiently utilized, and the transfer of its chiral centers was realized. Under the optimum condition, the corresponding lactones were successfully prepared from C4-C6 sugars with cyclic hemiacetal structure in acetonitrile. The reaction mechanism in acetonitrile was explored by the first principle density functional theory calculations and tracking reaction process. It was found that the high lactone yield in acetonitrile was due to the high proportion of α-conformation form among multiple tautomers in it. This selective dehydrogenation process may further extend the possibility of the preparation of chiral synthons from carbohydrates directly.
- Biomass,
- Cyclic hemiacetal sugars,
- Dehydrogenation,
- Chiral lactones,
- Conformation
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