Isoquinoline‐1‐Carboxylate as a Traceless Leaving Group for Chelation‐Assisted Glycosylation under Mild and Neutral Reaction Conditions

• DOI: 10.1002/anie.201708920
• Publication Date: 2017-10-19T15:46:40Z
• Authors: Hao‐Yuan Wang; Christopher J. Si...; Stephanie A. Blas...; Paul G. Balzer; Renshi Luo; Xiyan Duan; Weiping Tang
• Keywords: Carboxylate; Isoquinoline; Glycosyl donor

Abstract Glycosyl isoquinoline‐1‐carboxylate was developed as a novel benchtop stable and readily available glycosyl donor. The glycosylation reaction promoted by the inexpensive Cu(OTf) 2 salt under mild conditions. copper precipitated from solution thus rendered traceless leaving group. Surprisingly, proton acceptor absorbed metal complex mixture remained at neutral pH. copper‐promoted also proven to be completely orthogonal gold‐promoted glycosylation, an iterative synthesis of oligosaccharides anomeric ester building blocks becomes possible