An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-l-sugars |
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| Authors: | Qi Sun Xingjian Li Jian Sun Shanshan Gong Gang Liu Guodong Liu |
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| Affiliation: | 1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang, Jiangxi 330013, PR China;2. High Level Engineering Research Center of Biopharmaceutical Molecules and Diagnostic Apparatuses, Jiangxi Provincial Colleges and Universities, 605 Fenglin Avenue, Nanchang, Jiangxi 330013, PR China |
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| Abstract: | Four nucleoside diphosphate 6-deoxy-l-sugars have been efficiently synthesized by coupling sugar-1-phosphates prepared from the H-phosphonate precursors with nucleoside 5′-phosphoropiperidates in the presence of 4,5-dicyanoimidazole (DCI) as the activator. Compared to the conventional 1H-tetrazole-promoted phosphoromorpholidate method, the new phosphoropiperidate/DCI system significantly shortened the reaction time and afforded nucleoside diphosphate sugars in excellent isolated yields. |
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| Keywords: | Nucleoside diphosphate sugar H-Phosphonate Sugar-1-phosphate Phosphoropiperidate 4,5-Dicyanoimidazole |
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