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Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars
Author(s) -
Lim David,
Brimble Margaret A.,
Kowalczyk Renata,
Watson Andrew J. A.,
Fairbanks Antony John
Publication year - 2014
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.201406694
Subject(s) - glycoconjugate , chemistry , stereoselectivity , protecting group , cycloaddition , combinatorial chemistry , aqueous solution , hexafluorophosphate , glycoside , glycosylation , organic chemistry , alkyne , functional group , catalysis , biochemistry , ionic liquid , alkyl , polymer
The conversion of sugars into glycomimetics typically involves multiple protecting‐group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high‐yielding and stereoselective process is highly desirable. The combined use of 2‐azido‐1,3‐dimethylimidazolinium hexafluorophosphate and the Cu‐catalyzed Huisgen cycloaddition allowed the synthesis of a range of glycoconjugates in a one‐step reaction directly from reducing sugars under aqueous conditions. The reaction, which is completely stereoselective, may be applied to the convergent synthesis of triazole‐linked glycosides, oligosaccharides, and glycopeptides. The procedure provides a method for the one‐pot aqueous ligation of oligosaccharides and peptides bearing alkyne side chains.