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Isoquinoline‐1‐Carboxylate as a Traceless Leaving Group for Chelation‐Assisted Glycosylation under Mild and Neutral Reaction Conditions
Author(s) -
Wang HaoYuan,
Simmons Christopher J.,
Blaszczyk Stephanie A.,
Balzer Paul G.,
Luo Renshi,
Duan Xiyan,
Tang Weiping
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201708920
Subject(s) - chemistry , carboxylate , isoquinoline , glycosylation , anomer , glycosyl , salt (chemistry) , glycosyl donor , chelation , combinatorial chemistry , metal , polymer chemistry , medicinal chemistry , organic chemistry , biochemistry
Glycosyl isoquinoline‐1‐carboxylate was developed as a novel benchtop stable and readily available glycosyl donor. The glycosylation reaction was promoted by the inexpensive Cu(OTf) 2 salt under mild reaction conditions. The copper isoquinoline‐1‐carboxylate salt was precipitated from the solution and thus rendered a traceless leaving group. Surprisingly, the proton from the acceptor was absorbed by the precipitated metal complex and the reaction mixture remained at neutral pH. The copper‐promoted glycosylation was also proven to be completely orthogonal to the gold‐promoted glycosylation, and an iterative synthesis of oligosaccharides from benchtop stable anomeric ester building blocks becomes possible under mild reaction conditions.