(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

Kwok-Kong Mong*, Tapan Kumar Pradhan, Cheng-Hsin Chiu, Wei-Cheng Hung, Chao-Ju Chen, Yi-Fang Wang

*Corresponding author for this work

研究成果: Article同行評審


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.

頁(從 - 到)2179-2186
期刊Organic Chemistry Frontiers
出版狀態Published - 21 八月 2020