標題: | Low-Concentration 1,2-trans beta-Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis |
作者: | Chao, Chin-Sheng Li, Chen-Wei Chen, Min-Chun Chang, Shih-Sheng Mong, Kwok-Kong Tony 應用化學系 Department of Applied Chemistry |
關鍵字: | carbohydrates;glycosylation;neighboring-group effects;stereoselectivity;substrate concentration |
公開日期: | 2009 |
摘要: | This study develops an operationally easy, efficient, and general 1,2-trans beta-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent beta-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosylsubstrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans beta-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans beta-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant beta-(1 -> 6)-glucan trisaccharide, beta-linked Gb(3) and isoGb(3) derivatives. |
URI: | http://hdl.handle.net/11536/7895 http://dx.doi.org/10.1002/chem.200901119 |
ISSN: | 0947-6539 |
DOI: | 10.1002/chem.200901119 |
期刊: | CHEMISTRY-A EUROPEAN JOURNAL |
Volume: | 15 |
Issue: | 41 |
起始頁: | 10972 |
結束頁: | 10982 |
顯示於類別: | 期刊論文 |