Stereoselective Electro-2-deoxyglycosylation from Glycals

Miao Liu; Kai-Meng Liu; De-Cai Xiong; Hanyu Zhang; Tian Li; Bohan Li; Xianjin Qin; Jinhe Bai; Xin-Shan Ye

doi:10.1002/anie.202006115

Stereoselective Electro-2-deoxyglycosylation from Glycals

Angew Chem Int Ed Engl. 2020 Aug 24;59(35):15204-15208. doi: 10.1002/anie.202006115. Epub 2020 Jun 15.

Authors

Miao Liu¹, Kai-Meng Liu¹, De-Cai Xiong^{1

2}, Hanyu Zhang¹, Tian Li¹, Bohan Li¹, Xianjin Qin¹, Jinhe Bai¹, Xin-Shan Ye¹

Affiliations

¹ State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191, China.
² Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 27 Shanda Nanlu, Jinan, Shandong, 250100, China.

PMID: 32394599
DOI: 10.1002/anie.202006115

Abstract

We report a novel and highly stereoselective electro-2-deoxyglycosylation from glycals. This method features excellent stereoselectivity, scope, and functional-group tolerance. This process can also be applied to the modification of a wide range of natural products and drugs. Furthermore, a scalable synthesis of glycosylated podophyllotoxin and a one-pot trisaccharide synthesis through iterative electroglycosylations were achieved.

Keywords: 2-deoxyglycosides; carbohydrates; electrocatalysis; glycals; glycosylation.

Publication types

Research Support, Non-U.S. Gov't