公开(公告)号：US06982329B2

公开(公告)日：2006-01-03

申请号：US10744857

申请日：2003-12-22

申请人： David L. Burgoyne ,  Gueijun Ji ,  Eugene W. Kelleher ,  Nicholas D. Paschalides ,  Kishore Ramachandran ,  Yaping Shen ,  Yuanlin Zhou

发明人： David L. Burgoyne ,  Gueijun Ji ,  Eugene W. Kelleher ,  Nicholas D. Paschalides ,  Kishore Ramachandran ,  Yaping Shen ,  Yuanlin Zhou

IPC分类号： C07J21/00 ,  C07J11/00

CPC分类号： C07J53/00 ,  C07J1/0011 ,  C07J21/008 ,  C07J41/0038 ,  Y02P20/55

摘要： Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding α,β-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the α,β-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.

公开(公告)号：US06696580B2

公开(公告)日：2004-02-24

申请号：US10154432

申请日：2002-05-22

申请人： David L. Burgoyne ,  Gueijun Ji ,  Eugene W. Kelleher ,  Nicholas D. Paschalides ,  Kishore Ramachandran ,  Yaping Shen ,  Yuanlin Zhou

发明人： David L. Burgoyne ,  Gueijun Ji ,  Eugene W. Kelleher ,  Nicholas D. Paschalides ,  Kishore Ramachandran ,  Yaping Shen ,  Yuanlin Zhou

IPC分类号： C07J100

CPC分类号： C07J53/00 ,  C07J1/0011 ,  C07J21/008 ,  C07J41/0038 ,  Y02P20/55

摘要： Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding &agr;,&bgr;-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the &agr;,&bgr;-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.

摘要翻译： 使用碘化铜和叔丁基过氧化氢，含有环己烯部分的类固醇有效地氧化成相应的α，β-不饱和酮。 含有α，β-不饱和酮结构的类固醇化合物使用加氢硼烷试剂然后氧化后处理有效地转化为相应的邻位二醇，例如硼烷，接着是过硼酸钠。 苯甲酰基和取代的苯甲酰基是化合物中存在的羟基的优异保护基。