Total Synthesis and Structural Revision of Rebaudioside S, a Steviol Glycoside
- J Org Chem. 2020 Dec 18;85(24):15857-15871. doi: 10.1021/acs.joc.0c00442.
- 1. National Research Centre for Carbohydrate Synthesis, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, China.
The total synthesis of rebaudioside S, a minor steviol glycoside from the leaves of Stevia rebaudiana, was investigated via a modular strategy, culminating not only in the first and highly efficient synthesis of Reb-S and analogues thereof but also in the revision of the originally proposed structure. The modular strategy dictated the application of C2-branched disaccharide Yu donors to forge C-13 steviol glycosidic linkages, posing considerable challenges in stereoselectivity control. Through systematic investigations, the effect of the internal glycosidic linkage configuration on the glycosylation stereoselectivity of 1,2-linked disaccharide donors was disclosed, and the intensified solvent effect by the 4,6-O-benzylidene protecting group was also observed with glucosyl donors. Through the orchestrated application of these favorable effects, the stereoselectivity problems were exquisitely tackled.
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