| 一步法合成9-去氧-8a-氮杂-8a-同型红霉素A |
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| 引用本文： | 王建华,江志尧.一步法合成9-去氧-8a-氮杂-8a-同型红霉素A[J].合成化学,2010,18(2). |
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| 作者姓名： | 王建华 江志尧 |
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| 作者单位： | 重庆大学,生物工程学院,重庆,400044 |
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| 基金项目： | 国家科技支撑计划，重庆市科技攻关项目 |
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| 摘 要： | 以(9Z)-9-去氧-9-羟基亚胺基红霉素A为原料,甲醇/水为反应体系,对甲苯磺酰氯为催化剂,硼氢化钠为还原剂,首次用一步法合成了9-去氧-8a-氮杂-8a-同型红霉素A,其结构经1H NMR和FAB-MS表征。在pH8~9,于-3℃反应9 h的较佳反应条件下,收率94.1%,纯度93.0%。
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| 关 键 词： | (9Z)-9-去氧-9-羟基亚胺基红霉素A 9-去氧-8a-氮杂-8a-同型红霉素A 贝克曼重排 一步法 药物合成 Beckmann′s rearrangement |
Synthesis of 9-Deoxo-8a-aza-8a-homoerythromycin A by One-step |
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| WANG Jian-hua,JIANG Zhi-yao.Synthesis of 9-Deoxo-8a-aza-8a-homoerythromycin A by One-step[J].Chinese Journal of Synthetic Chemistry,2010,18(2). |
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| Authors: | WANG Jian-hua JIANG Zhi-yao |
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| Abstract: | One-step method was applied to the synthesis of 9-deoxo-8a-aza-8a-homoerythromycin A for the first time from (9Z)-9-deoxo-9-hydroxyiminoerythromycin A by Beckmann's rearrangement using methanol/water as the solvent, p-toluene sulfonyl chloride as the catalyst, and sodium borohydride as the reductant. The structure was characterized by ~1H NMR and FAB-MS. The yield was 94.1% with purity 93.0% by the reaction at -3 ℃ for 9 h in solution of pH 8～9. |
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| Keywords: | (9Z)-9-deoxo-9-hydroxyiminoerythromycin A 9-deoxo-8a-aza-8a-homoerythromycin A one-step drug synthesis |
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