Citation: Gefei Li, Yanlong Luo, Juan Mo, Masato Noguchi, Jie Jing, Zhenyang Luo, Shin-ichiro Shoda, Xin-Shan Ye. Hydrogen bond-assisted 1, 2-cis O-glycosylation under mild hydrogenolytic conditions[J]. Chinese Chemical Letters, ;2023, 34(4): 107754. doi: 10.1016/j.cclet.2022.107754 shu

Hydrogen bond-assisted 1, 2-cis O-glycosylation under mild hydrogenolytic conditions

Gefei Li ^{a, b, c} ,
Yanlong Luo ^a ,
Juan Mo ^b ,
Masato Noguchi ^c ,
Jie Jing ^a ,
Zhenyang Luo ^a ,
Shin-ichiro Shoda ^{c, *,} ,
Xin-Shan Ye ^{b, *,}

a.
College of Science, Nanjing Forestry University, Nanjing 210037, China
b.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
c.
Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, Sendai 980-8579, Japan

shinichiro.shoda.a6@tohoku.ac.jp

xinshan@bjmu.edu.cn

Received Date: 17 June 2022
Revised Date: 10 August 2022
Accepted Date: 16 August 2022
Available Online: 18 August 2022

Figures(3)

A hydrogen bond-assisted α-selective glycosylation reaction by using 4, 6-dibenzyloxy-1, 3, 5-triazin-2-yl (DBT) β-glycosyl donors was developed for the efficient construction of 1, 2-cis-α-glycosidic bond in natural products. This method was applied successfully to the direct synthesis of complex oligosaccharide-derived glycolipids with simple protecting chemistry. Mechanistic studies using the NMR spectroscopy and DFT calculation provide a proof of concept for hydrogen bond-assisted glycosylation reaction towards α-specific construction of O-glycosidic linkage.
- O-Glycosylation,
- Hydrogen bond,
- α-Selectivity,
- Glycolipid,
- Natural product
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