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Fluorine‐Directed Glycosylation
Author(s) -
Bucher Christoph,
Gilmour Ryan
Publication year - 2010
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.201004467
Subject(s) - oxonium ion , glycosylation , anomer , chemistry , fluorine , glycosyl , computer science , scheme (mathematics) , glycosyl donor , combinatorial chemistry , stereochemistry , ion , organic chemistry , mathematics , biochemistry , mathematical analysis
Everything's under control : A stabilizing fluorine electrostatic interaction has been exploited to control oxonium ion conformation in 2‐fluoropyranose derivatives (see scheme). When matched with the inductive nature of the protecting groups, the glycosyl donors were found to be highly selective (2‐F Gluc /benzyl → β; 2‐F Manno /pivaloyl → α) leading to fluoro‐glycostructures with excellent control over the anomeric configuration.