Radical C-Glycosylation Using Photoexcitable Unprotected Glycosyl Borate

被引：3

作者：

Miyamoto, Yusuke ^{[1
]}

Murakami, Sho ^{[1
]}

Sumida, Yuto ^{[2
]}

Hirai, Go ^{[3
]}

Ohmiya, Hirohisa ^{[1
]}

机构：

[1] Inst Chem Res Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan

[2] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Lab Chem Biosci, Kanda Surugadai,Chiyoda Ku, Tokyo 1010062, Japan

[3] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 51期

关键词：

C-glycosylation; Radical; Glycosyl borate; Visible light; STEREOSELECTIVE-SYNTHESIS; 2-TRIFLUOROBORATOCHROMANONES;

D O I：

10.1002/chem.202402256

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We 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. We 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-glycoside. image

引用

页数：5

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