Volume 132, Issue 35 pp. 15316-15320
Zuschrift

Stereoselective Electro-2-deoxyglycosylation from Glycals

Miao Liu

Miao Liu

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

These authors contributed equally to this work.

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Kai-Meng Liu

Kai-Meng Liu

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

These authors contributed equally to this work.

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Dr. De-Cai Xiong

Corresponding Author

Dr. De-Cai Xiong

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 27 Shanda Nanlu, Jinan, Shandong, 250100 China

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Hanyu Zhang

Hanyu Zhang

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

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Tian Li

Tian Li

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

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Bohan Li

Bohan Li

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

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Xianjin Qin

Xianjin Qin

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

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Jinhe Bai

Jinhe Bai

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

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Prof. Xin-Shan Ye

Corresponding Author

Prof. Xin-Shan Ye

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China

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First published: 11 May 2020
Citations: 13

Dedicated to Professor Henry N. C. Wong on the occasion of his 70th birthday

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.

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