Premium
S ‐Adamantyl Group Directed Site‐Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides
Author(s) -
Blaszczyk Stephanie A.,
Xiao Guozhi,
Wen Peng,
Hao Hua,
Wu Jessica,
Wang Bo,
Carattino Francisco,
Li Ziyuan,
Glazier Daniel A.,
McCarty Bethany J.,
Liu Peng,
Tang Weiping
Publication year - 2019
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.201903587
Subject(s) - acylation , chemistry , glycosylation , steric effects , stereochemistry , oligosaccharide , glycoside , cationic polymerization , combinatorial chemistry , catalysis , organic chemistry , biochemistry
The site‐selective functionalization of carbohydrates is an active area of research. Reported here is the surprising observation that the sterically encumbered adamantyl group directed site‐selective acylation at the C2 position of S ‐glycosides through dispersion interactions between the adamantyl C−H bonds and the π system of the cationic acylated catalyst, which may have broad implications in many other chemical reactions. Because of their stability, chemical orthogonality, and ease of activation for glycosylation, the site‐selective acylation of S ‐glycosides streamlines oligosaccharide synthesis and will have wide applications in complex carbohydrate synthesis.