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Synthetic Access Toward Cycloastragenol Glycosides

Ting Liu¹, Jin-Xi Liao¹, Yang Hu¹

¹The National Research Centre for Carbohydrate Synthesis, Jiangxi Normal University , 99 Ziyang Avenue, Nanchang 330022, China.

The Journal of Organic Chemistry

|March 28, 2017

Abstract:

The first efficient synthetic approach toward four types of the cycloartane glycosides, the cycloastragenol 25-O; 3-O; 3,6-O-bis; and 3,25-O-bisglycoside, have been established, which featured the PPY-mediated, concentration-controlled acetylation and Au(I)-catalyzed Yu glycosylation. Through the synthetic investigation, the reactivity sequence of the four OHs in cycloastragenol was fixed for the first time and a detour strategy for the highly efficient removal of bulky pivaloyl protecting groups was discovered.

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