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Dimethylformamide: An Unusual Glycosylation Modulator
Author(s) -
Lu ShaoRu,
Lai YenHsun,
Chen JiunHan,
Liu ChihYueh,
Mong KwokKong Tony
Publication year - 2011
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.201100076
Subject(s) - glycosylation , chemistry , stereoselectivity , dimethylformamide , combinatorial chemistry , scheme (mathematics) , simple (philosophy) , computer science , organic chemistry , biochemistry , catalysis , epistemology , mathematics , philosophy , solvent , mathematical analysis
A simple solution : When N , N ‐dimethylformamide was used to direct the stereochemical course of glycosylation reactions, 1,2‐ cis glycosylation products were formed with excellent selectivity. A straightforward highly α‐stereoselective glycosylation involving preactivation (see scheme) should find broad application and be especially useful for sequential glycosylation reactions to form oligosaccharides. LG=leaving group.