Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis | Zendy

Smoot James T. | Zendy; Pornsuriyasak Papapida | Zendy; Demchenko Alexei V. | Zendy

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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.

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