Recent advances in glycosylation involving novel anomeric radical precursors

Abstract

Radical glycosylation has gradually become a powerful and effective method to synthesize carbohydrate mimetics as reactions via radical intermediates usually provide excellent functional group compatibility and good anomeric selectivity. Novel glycosyl radical precursors have been identified as glycosyl donors in radical glycosylation to access C-, S- and Se-glycosides. This review aims at summarizing the remarkable advances in radical glycosylation reactions to illuminate potential future research directions. Herein, the most recent literature concerning radical glycosylation is covered with a specific emphasis on radical precursor design along with discussions of consequential mechanisms.

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Keywords:

• Carbohydrate mimetics
• glycosyl precursors
• glycosylation
• radical reactions

Author contributions

The manuscript was written with contributions from all authors. Each author has approved the final version of the manuscript.

Disclosure statement

The authors declare no competing financial interest.

Additional information

Funding

This work was sponsored by the Shanghai Sailing Program [21YF1420600]; Natural Science Foundation of Shanghai [21ZR1435600]; and startup fundings from Shanghai Jiao Tong University [AF1100077/008 and WH220432508].

Notes on contributors

Tianyi Yang

  Dr. Tianyi Yang received both B.S. and M.S. degrees in Pharmaceutical Sciences from Sun Yat-sen University and University of Pittsburgh, respectively. After that, he switched major to Organic Chemistry and obtained his Ph.D. degree from University of Colorado Boulder in 2019. He then joined the Research and Development department in Corden Pharma Colorado as a senior process chemist where he continued to bring the enthusiasm and expertise in synthetic organic chemistry and medicinal chemistry on board and lead multifunctional teams to develop solutions for the industrial manufacturing of pharmaceutical products.

Feng Zhu

  Prof. F. Zhu received his B.S. degree in Applied Chemistry from Guangxi University in 2010. After receiving his Ph.D. degree in 2015 from UniversityofScienceand Technology of China under the supervision of Prof. Zhong-Xia Wang, he joined Prof. Maciej Walczak’s group at University of Colorado Boulder. In 2021, he started his independent career as an Associate Professor in Frontiers Science Center for Transformative Molecules at Shanghai Jiao Tong University. Prof. Zhu?s has focused his research interest on the development of novel and efficient strategies for the synthesizing carbohydrates, peptides, and other small molecules with important chemical biological properties. He leverages his expertise in organic chemistry to address the present-day problems in the study of chemistry, biology, and medicine.