The synthesis of nebularine and its analogs via oxidative desulfuration in aqueous nitric acid |
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| Authors: | Ran Xia Li-Ping Sun Gui-Rong Qu |
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| Institution: | 1. School of Chemistry and Chemical Engineering, School of Life Science and Technology, Xinxiang University, Xinxiang City, Henan Province, Chinaranxia518@hotmail.com;3. School of Chemistry and Chemical Engineering, School of Life Science and Technology, Xinxiang University, Xinxiang City, Henan Province, China;4. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang City, Henan Province, China |
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| Abstract: | The synthesis of nebularine and its analogs has been achieved via oxidative desulfuration in H2O for the first time. With 50% HNO3 as an oxidant and solvent, 18 products were obtained in good yields (70%–94%). The oxidative desulfuration system could tolerate different functional groups including fluoro, chloro, amino, alkyl, allyl, ribosyl, deoxyribosyl, and arabinofuranosyl groups. More importantly, the drug nebularine could be obtained successfully on a 20 g scale, which made this route more attractive for industrial applications. |
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| Keywords: | Nebularine desulfuration base modification nucleoside synthesis |
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