Premium
Chemoselective Iterative Dehydrative Glycosylation
Author(s) -
Nguyen Hien M.,
Poole Jennifer L.,
Gin David Y.
Publication year - 2001
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 - 10.1002/1521-3773(20010119)40:2<414::aid-anie414>3.0.co;2-6
Subject(s) - glycosylation , anomer , nucleophile , computer science , chemistry , scheme (mathematics) , combinatorial chemistry , group (periodic table) , theoretical computer science , stereochemistry , organic chemistry , biochemistry , mathematics , catalysis , mathematical analysis
The inherent difference in nucleophilicity between alkyl alcohols and free hemiacetals is capitalized upon in a new approach to chemoselective glycosylation. The strategy employs a controlled dehydrative coupling reaction for the rapid assembly of complex oligosaccharides and obviates the need for the extensive protective group and anomeric leaving group differentiation that is traditionally required (see scheme).