Recent development in additive modulated stereoselective glycosidation reactions

Abstract

Stereoselective glycosidic bond formation (termed “glycosidation”) remains a challenge in carbohydrate chemistry. Despite such difficulty, a variety of innovative strategies have been developed. In particular, additive-modulated stereoselective construction of glycosidic linkages has become an emerging trend. In this review, we summarized the recent progress in this area with respect to common glycosyl donors, including thioglycosides, glycosyl imidates, glycosyl acetates, glycosyl hemiacetals, glycosyl phosphates and glycosyl ortho-alkynylbenzoates. Together with their merits/limitations, these achievements shed light on carbohydrate chemistry and enabled the efficient preparation of complex oligosaccharides and glycoconjugates.

Graphical Abstract

Keywords:

• Additive controlled
• carbohydrate
• glycosidation
• stereoselective

Additional information

Funding

This work is financially supported by National Natural Science Foundation of China [Grant No. 92053110], China Postdoctoral Science Foundation [2020M680090], the Fundamental Research Funds of Shandong University [2019HW034], and the Qilu Youth Scholar Program of Shandong University, Open Projects Funds of Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University [No. 2021CCG01 &02], the Central Government Guide Local Science and Technology Development Funds [YDZX20203700002579].

Notes on contributors

Peng Peng

Prof. P. Peng received his B.S. degree in chemistry from Lanzhou University in 2006. In 2011, he received his Ph.D. degree from Peking University under the supervision of Prof. Xin-shan Ye. Then he joined the group of Prof. Xuechen Li at the University of Hong Kong as a Research Associate. From 2014 to 2016, Dr. Peng had a postdoctoral fellowship with Prof. Dr. Richard R. Schmidt at the University of Konstanz. In 2016, he started his independent career as a tenue-track Professor in National Glycoengineering Research Center at Shandong University, and was promoted as a full Professor in 2018. Prof. Peng?s major research interest is in the field of carbohydrate chemistry, the development of novel strategies and synthesis of complex oligosaccharides and glycoconjugates.