| 泰利霉素重要中间体3-氧代-6-O-甲基红霉素的合成 |
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| 引用本文： | 李树宾,孟涛,姚国伟,闫建辉,罗爱芹.泰利霉素重要中间体3-氧代-6-O-甲基红霉素的合成[J].精细化工,2007,24(7):678-680. |
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| 作者姓名： | 李树宾 孟涛 姚国伟 闫建辉 罗爱芹 |
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| 作者单位： | 北京理工大学,生命科学与技术学院,北京,100081 |
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| 基金项目： | 国家经贸委技术创新项目 |
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| 摘 要： | 由克拉霉素的前体6-O-甲基-2′,4″-二(三甲基硅)-红霉素A9-(1-异丙氧基环己基)肟(Ⅰ)出发,常温下以φ(HC l)=10%的盐酸催化水解得3-羟基-6-O-甲基红霉素A9肟(Ⅱ);然后一锅煮进行化合物Ⅱ的2′-羟基乙酰化、3-羟基氧化,得2′-乙酰基-3-氧代-6-O-甲基红霉素A9-(O-乙酰基)肟(Ⅳ);最后脱乙酰基、还原9-肟基再次应用一锅煮法合成,得到目的化合物3-氧代-6-O-甲基红霉素(Ⅵ),总收率为57.0%,经HPLC测定w(Ⅵ)=98.5%。通过1HNMR1、3CNMR和MS,表征了各中间体及目标化合物的结构。
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| 关 键 词： | 3-氧代-6-O-甲基红霉素 泰利霉素 一锅煮 医药原料 |
| 文章编号： | 1003-5214（2007）07-0678-03 |
| 修稿时间： | 2006-12-202007-02-28 |
Synthesis of 3-Oxo-6-O-methylerythromycin,an Important Intermediate of Telithromycin |
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| LI Shu-bin,MENG Tao,YAO Guo-wei,YAN Jian-hui,LUO Ai-qin.Synthesis of 3-Oxo-6-O-methylerythromycin,an Important Intermediate of Telithromycin[J].Fine Chemicals,2007,24(7):678-680. |
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| Authors: | LI Shu-bin MENG Tao YAO Guo-wei YAN Jian-hui LUO Ai-qin |
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| Affiliation: | School of Life Science and Technology, Beifing Institute of Technology, Beijing 100081, China |
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| Abstract: | Hydrolysis of 6-O-methyl-2′,4″-bis(trimethylsilyl)-erythromycin A9-(isopropoxycyclohexyl) oxime,a precursor of clarithromycin,was conducted under φ(HCl)=10% hydrochloric acid as a catalyst at room temperature for 2 h to yield 3-hydroxy-6-O-methylerythromycin A9-oxime.Then 2′-OH was protected with acetyl group and 3-OH was oxidized in one-pot synthesis to yield 2′-O-acetyl-3-oxo-6-O-methylerythromycin A9-acetyloxime.Finally two acetyl groups were removed and 9-oxime was reduced in one-pot synthesis.3-Oxo-6-O-methylerythromycin was obtained in 57.0% overall yield with 98.5% purity.Structures of the target compound and all intermediates were identified by 1HNMR,13CNMR and MS. |
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| Keywords: | 3 -oxo-6 -O-methylerythromycin telithromycin one-pot synthesis drug materials |
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