6-(3-Cyanopropyl)-2-vinyl tetrahydropyran-2-ol and its tautomer
    6.
    发明授权
    6-(3-Cyanopropyl)-2-vinyl tetrahydropyran-2-ol and its tautomer 失效
    6-(3-氰基丙基)-2-乙烯基四氢吡喃-2-醇及其互变异构体

    公开(公告)号:US3994930A

    公开(公告)日:1976-11-30

    申请号:US613675

    申请日:1975-09-15

    摘要: A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents .gamma.-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting the protective groups as was heretofore found necessary in previous steroid total synthesis processes.

    摘要翻译: 公开了使用具有氰基烷基A环前体的中间体的多步立体定向全合成类固醇。 该方法的初始起始原料是相对便宜且市售的试剂γ-丁内酯和氰化钠。 该方法适用于制备外消旋或光学活性的药用价值类固醇,特别是19-降胆固醇。 该方法的特征在于,选择在多步合成期间使用的条件,以便即使在氢化和水解步骤期间也保持正常不稳定的腈基。 以这种方式,可以使用腈基作为A环前体,而不必诉诸于以前在以前的类固醇总合成方法中必需的保护基。