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Unusually Stable Picoloyl‐Protected Trimethylsilyl Glycosides for Nonsymmetrical 1,1′‐Glycosylation and Synthesis of 1,1′‐Disaccharides with Diverse Configurations
Author(s) -
Lu YenChu Luke,
Ghosh Bhaswati,
Mong KwokKong Tony
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700785
Subject(s) - glycosylation , glycoside , chemistry , stereochemistry , stereoselectivity , combinatorial chemistry , organic chemistry , catalysis , biochemistry
Nonsymmetrical 1,1′‐disaccharides and related derivatives constitute structural components in various glycolipids and natural products. Some of these compounds have been shown to exhibit appealing biological properties. We report a direct yet stereoselective 1,1′‐glycosylation strategy for the synthesis of nonsymmetrical 1,1′‐disaccharides with diverse configurations and sugar components. The strategy is based on the joined forces of a new class of configurationally stable glycoside acceptors and stereodirecting thioglycoside donors. The new glycoside acceptors feature a picoloyl (Pico) protecting group at the remote C4/C3 position that confers unusual stability on TMS glycosides under acidic conditions.