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Frontispiece: Assembly of a Complex Branched Oligosaccharide by Combining Fluorous‐Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions
Author(s) -
Huang Wei,
Gao Qi,
Boons GeertJan
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201583762
Subject(s) - stereoselectivity , anomer , sulfonium , glycosyl , chemistry , glycosylation , glycoside , oligosaccharide , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , catalysis , salt (chemistry)
Stereoselective Glycosylations. In their Full Paper on page 12920 ff. , G.‐J. Boons et al. demonstrate that a set of strategically selected orthogonal protecting groups, that is, glycosyl donors modified by a chiral auxiliary and glycosyl acceptors containing a fluorous tag, make it possible to rapidly prepare complex branched oligosaccharides of biological importance. After the glycosylations, the chiral auxiliary could be removed using moderately strong acidic conditions, which were compatible with the presence of the orthogonal protecting groups, thereby allowing efficient installation of 1,2‐ cis ‐linked glycosides.