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角鲨多胺重要中间体的合成

Synthesis of Key Intermediates of Squalamine
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摘要 以3β-乙酰氧基-7α-甲氧基亚甲氧基-5α-胆烷酸甲酯(1)为原料,经二异丁基氢化铝还原得3β-羟基-7α-甲氧基亚甲氧基-24-醛基-5α-胆甾烷(2);2依次经二氢吡喃保护、格氏试剂对24-位醛基的不对称加成,合成了角鲨多胺的重要中间体——3β-四氢吡喃氧基-7α-甲氧基亚甲氧基-24(R)-羟基-5α-胆甾烷,其结构经1H NMR,13C NMR,IR和MS确证。 3β-hydroxy-7α-methoxymethyleneoxy-24-al-5α-cholestane（2） was obtained by direct reduction of methyl 3β-acetoxy-7α-methoxymethyleneoxy-5α-cholanate（1） using diisobutyl aluminum hydride as the reducing agent.A key intermediate of Squalamine,3β-tetrahydropyran-7α-methoxymethyleneoxy-24（R）-hydroxy-5α-cholestane,was synthesized by dihydropyran protection and asymmetric addition of passivated Grignard reagent to carbonyl group of 2.The structures were confirmed by 1H NMR,13C NMR,IR and MS.
作者 江宁 陈书艳 宋琦 张莉莉 史海健
机构地区 南京工业大学化学化工学院
出处 《合成化学》 CAS CSCD 北大核心 2013年第4期508-512,共5页 Chinese Journal of Synthetic Chemistry
关键词 角鲨多胺 中间体 格氏试剂 不对称合成 Squalamine intermediate Grignard reagent asymmetric synthesis
分类号 O621.3 [理学—有机化学] R914.5 [医药卫生—药物化学]
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参考文献9

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合成化学
2013年 第4期

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