Radical C‐Glycosylation Using Photoexcitable Unprotected Glycosyl Borate

Author:

Miyamoto Yusuke1,Murakami Sho1,Sumida Yuto2,Hirai Go3,Ohmiya Hirohisa1ORCID

Affiliation:

1. Institute for Chemical Research Kyoto University 611-0011 Gokasho, Uji, Kyoto Japan

2. Laboratory of Chemical Bioscience Institute of Biomaterials and Bioengineering Tokyo Medical and Dental University 101-0062 Kanda- Surugadai, Chiyoda-ku Tokyo Japan

3. Graduate School of Pharmaceutical Sciences Kyushu University 812-8582 Maidashi, Higashiku, Fukuoka Japan

Abstract

AbstractWe have developed radical C‐glycosylation using photoexcitable unprotected glycosyl borate. The direct excitation of glycosyl borate under visible light irradiation enabled the generation of anomeric radical without any photoredox catalysts. The in situ generated anomeric radical was applicable to the radical addition such as Giese‐type addition and Minisci‐type reaction to introduce alkyl and heteroaryl groups at the anomeric position. In addition, the radical–radical coupling between the glycosyl borate and acyl imidazolide provided unprotected acyl C‐glycosides.

Funder

Japan Society for the Promotion of Science

Japan Science and Technology Agency

Publisher

Wiley

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