Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-d-glucopyranosylorthoesters strategy |
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| Authors: | Guangfa Wang Zhichao Lu Ning Ding Wei Zhang Peng Wang Yingxia Li |
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| Institution: | aSchool of Pharmacy, Fudan University, Shanghai 201203, China;bCollege of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China;cSchool of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China |
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| Abstract: | A facile and efficient method to differentiate the 2,3-diols of glucopyranosides based on 1,2-orthoesters strategy was developed. Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters. When treated with HCl aqueous solution and followed with Et3N, differentiation of the 2,3-diols was efficiently achieved along with the generation of a convertible anomeric hydroxyl group. In addition, an easy and practical method based on NOE was proposed to determine whether the 1,2-orthoesters were endo-type or exo-type. |
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| Keywords: | 1 2-Orthoesters 2 3-Diols Thioglucoside endo-Type exo-Type |
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