標題: Unusually Stable Picoloyl-Protected Trimethylsilyl Glycosides for Nonsymmetrical 1,1-Glycosylation and Synthesis of 1,1-Disaccharides with Diverse Configurations
作者: Lu, Yen-Chu Luke
Ghosh, Bhaswati
Mong, Kwok-Kong Tony
應用化學系
Department of Applied Chemistry
關鍵字: carbohydrates;donor-acceptor systems;glycosides;glycosylation;protecting groups
公開日期: 1-May-2017
摘要: 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.
URI: http://dx.doi.org/10.1002/chem.201700785
http://hdl.handle.net/11536/145523
ISSN: 0947-6539
DOI: 10.1002/chem.201700785
期刊: CHEMISTRY-A EUROPEAN JOURNAL
Volume: 23
起始頁: 6905
結束頁: 6918
Appears in Collections:Articles