A general approach to C-Acyl glycosides via palladium/copper Co-catalyzed coupling reaction of glycosyl carbothioates and arylboronic acids. (26th February 2021)

• Record Type: Journal Article
• Authors: Wang, Li-Na; Niu, You-Hong; Cai, Qing-Hui; Li, Qin; Ye, Xin-Shan
• Is Part Of: Tetrahedron. Volume 82(2021)
• Publication Date: 2021-02-26
• Subjects: C-Acyl glycoside -- Glycosyl carbothioate -- Arylboronic acid -- Liebeskind–srogl cross-coupling reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.131955
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A general and efficient approach to the synthesis of various C -acyl glycosides has been developed via Pd2 (dba)3 /CuTC co-catalyzed cross-coupling reaction of glycosyl carbothioates with arylboronic acids. The reaction showed a broad substrate scope and 25 examples were exhibited in 61%–97% isolated yields. Furthermore, this reaction was applied to the gram-scale preparation of C -acyl glycosides. The coupled products can be further transformed into diverse biologically useful compounds, as exemplified by the synthesis of protected sergliflozin-A mimics. Graphical abstract: Image 1