Stereoselective glycosylation with conformation-constrained 2-Nitroglycals as donors and bifunctional thiourea as catalyst

Abstract

Herein, we report a novel method for highly efficient and stereoselective construction 1,2-cis-2-amino-2-deoxy-glycosidic linkages using conformation-constrained 2-nitroglycal donors and bifunctional thiourea catalyst. The method enjoys mild reaction conditions, good to excellent stereoselectivity, broad substrate scope, and good to excellent efficiency.

Graphical Abstract

Keywords:

• 2-amino-2-deoxyglycosides
• conformation-constrained donor
• 2-nitroglycal
• organocatalysis
• stereoselective glycosylation

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was financially supported by the National Natural Science Foundation of China [21977039, 21877055, 21762024, 22007039 and 22167015].

Notes on contributors

Jian-Song Sun

Prof. Jian-Song Sun received his B.Sc. in chemistry from Qufu Normal University in 2000 and Ph.D. from Dalian Institute of Chemical Physics, Chinese Academy of Science, in 2005 (with Prof. B. Yu and X. Han). He then joined Prof. R. R. Schmidt?s group at Konstanz University as a Humboldt postdoctoral fellow. In 2007, he returned to Shanghai Institute of Organic Chemistry as an associate research professor. In 2014, he moved to Jiangxi Normal University and was promoted to research professor. His research interests include carbohydrate chemistry and carbohydrate-based therapeutics.

Qingju Zhang

Prof. Q. Zhang completed his M.S. studies at Zhengzhou University and Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, supervised by Prof. Biao Yu, Prof. Fuyi Zhang and Prof. Jiansong Sun in 2011. Then he continued his research work in Prof. Yu Group as research associate until 2013. He completed his PhD and Postdoc research at Leiden University, under the supervision of Prof. G. A. van der Marel and Prof. J. D. C. CodÅe in 2018. After that, he started his independent career as a Full Professor in National Research Centre for Carbohydrate Synthesis at Jiangxi Normal University. His major research interest includes carbohydrate synthetic methodology and total synthesis of oligosaccharides and glycoconjugates for carbohydrate-based vaccine and glycodrug development.