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-Aug-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
Appears in Collections:Articles