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Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis
Author(s) -
Smoot James T.,
Pornsuriyasak Papapida,
Demchenko Alexei V.
Publication year - 2005
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.200502694
Subject(s) - moiety , glycosylation , glycosyl , stereoselectivity , glycosidic bond , glycosyltransferase , chemistry , linkage (software) , stereochemistry , group (periodic table) , oligosaccharide , combinatorial chemistry , biochemistry , organic chemistry , catalysis , gene , enzyme
Armed and dangerous : A new armed–disarmed glycosylation strategy (see picture) allows chemoselective introduction of a 1,2‐ trans glycosidic linkage prior to other linkages through the use of a 2‐ O ‐picolyl moiety. This neighbouring group is capable of efficient participation through a six‐membered intermediate while retaining the glycosyl donor in the armed state. Bn=benzyl, Bz=benzoyl, Tf=trifluoromethanesulfonyl, Pic=picolyl.