Practical synthesis of 2-deoxy sugars via metal free deiodination reactions

Abstract

2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction by using cyclohexane and ethyl acetate as co-solvent is reported. This is an environmentally benign protocol, which operates smoothly under mild conditions and allows efficient preparation of a series of 2-deoxy-glycosides in up to 98% yields.

Graphical Abstract

Keywords:

• Carbohydrate
• 2-deoxy-glycosides
• deiodination
• dilauroyl peroxide
• hydron atom abstraction

Acknowledgments

The authors thank National Natural Science Foundation of China (21877043, 22025102, 21772050), the Fundamental Research Funds for the Central Universities, HUST (2019kfyXKJC080, 2019JYCXJJ046) and Huazhong University of Science and Technology for financial support. Analytical and Testing Center of HUST for NMR tests is appreciated.

Additional information

Notes on contributors

Jing Zeng

Prof. J. Zeng received his B.Eng. degree from Southeast University in 2004 and M.S. degree from Xiamen University in 2007 under the supervision of Prof. Anqi Chen and Prof. Hongkui Zhang. He completed his PhD studies in 2013 at the Nanyang Technological University, supervised by Prof. Xue-Wei Liu. He joined the School of Pharmacy at the Huazhong University of Science and Technology as associate professor in 2014 and was promoted as professor in 2018. His current research interests focus on the chemistry and biochemistry of rare sugars.

Qian Wan

Prof. Q. Wan received his B.S. degree in chemistry from Central China Normal University in 1997. In 2000, he completed his M.S. studies at the Paris-Sud University, supervised by Prof. Claudine AugÅ. After receiving his Ph.D. degree in 2004 from the Paris-Sud University under the supervision of Prof. André Lubineau and Prof. Marie-Christine Scherrmann, he joined the group of Prof. Samuel J. Danishefsky at the Memorial Sloan-Kettering Cancer Center as a postdoctoral fellow. From 2007 to 2011, Dr. Wan was a scientist at Amgen Inc. In 2012, he started his independent career as a full professor in Tongji School of Pharmacy at Huazhong University of Science and Technology. Prof. Wan’s major research interests focus on the development of novel and efficient strategies for the synthesis of biologically important oligosaccharides and the discovery of new free radical chemistry.