標題: | (2-Ketulosonyl)onate 2,3-O-thionocarbonate donors for the synthesis of KO and KDO alpha-glycosides and a one-pot glycosylation method for 2-keto acid donors |
作者: | Mong, Kwok-Kong Tony Pradhan, Tapan Kumar Chiu, Cheng-Hsin Hung, Wei-Cheng Chen, Chao-Ju Wang, Yi-Fang 應用化學系 Department of Applied Chemistry |
公開日期: | 21-八月-2020 |
摘要: | We report a short synthetic strategy for direct preparation of (2-ketulosonyl)onate donors. These donors feature a cyclic thionocarbonate group at the C2 and C3 positions, which plays a multitude of chemical roles. It protects the C2 and C3 hydroxyls during building block preparation. In glycosylation, the thionocarbonate can be activated by a sulfenylating promoter and serves as a leaving group. Because of its beta-configuration, it also plays the role of a stereo-directing group during the formation of the alpha-glycosidic bond. In addition, the thionocarbonate donors can couple with thioglycoside acceptors. This orthogonal property was used for the development of the first one-pot glycosylation method for 2-keto acid sugars. |
URI: | http://dx.doi.org/10.1039/d0qo00630k http://hdl.handle.net/11536/155119 |
ISSN: | 2052-4129 |
DOI: | 10.1039/d0qo00630k |
期刊: | ORGANIC CHEMISTRY FRONTIERS |
Volume: | 7 |
Issue: | 16 |
起始頁: | 2179 |
結束頁: | 2186 |
顯示於類別: | 期刊論文 |