Additive-controlled synthesis of 1- and 2-deoxysugars from thioglycosides

Abstract

Two photoreactions for the synthesis of 1- and 2-deoxysugars from thioglycosides were developed. In the presence of Hantzsch ester as an additive, a wide range of 1-deoxysugars were synthesized in moderate to excellent yields under irradiation with UV light without an exogenous photosensitizer. On the other hand, the utilization of 2,4,6-tri-tert-butylpyrimidine (TTBP) as the additive furnished a variety of 2-deoxysugars as the main products from their corresponding thioglycosides. The reported methodology has a broad substrate scope and high functional group tolerance and is scalable to gram-scale reaction.

Graphical Abstract

Keywords:

• Thioglycoside
• deoxysugar
• hantzsch ester
• 2,4,6-tri-tert-butylpyrimidine
• glycosyl radical
• photoreaction

Correction Statement

This article has been corrected with minor changes. These changes do not impact the academic content of the article.

Additional information

Funding

This research was funded by grants from the National Natural Science Foundation of China [Grant No. 21772006], the open fund of State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, China [Grant no. KF-GN-202106], and the Fundamental Research Funds for the Central Universities.

Notes on contributors

De-Cai Xiong

Dr. D. Xiong received his B.S. degree in chemistry from Lanzhou University in 2005. He obtained his Ph.D. degree from Peking University in 2010 under the supervision of Prof. Xin-Shan Ye. He then joined in School of Pharmaceutical Sciences at Peking University as a lecturer. Presently he is working as an assistant professor at Peking University. His research interests mainly focus on photo-/electro-driven glycochemistry and the synthesis of oligosaccharides and polysaccharides.