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: | 1-五月-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 |
顯示於類別: | 期刊論文 |