(3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-10-eth-(Z)-ylidene-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthrene | 871247-59-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-10-eth-(Z)-ylidene-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthrene
• 英文别名: tert-butyl-[[(1S,2R,6R,7S,9S,12S,13S,14S,16S,17Z,20S)-17-ethylidene-4,4,12,16-tetramethyl-14-triethylsilyloxy-3,5-dioxapentacyclo[11.7.0.02,6.07,12.016,20]icosan-9-yl]oxy]-dimethylsilane
• CAS: 871247-59-5
• 化学式: C₃₆H₆₆O₄Si₂
• 分子量: 619.089
• InChiKey: JTXVCFWTIOHSIO-QFFIXKFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.11
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-10-eth-(Z)-ylidene-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthrene 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-10-eth-(E)-ylidene-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-11-one
  参考文献：
  名称：

  The Synthesis and Preliminary Biological Evaluation of a Novel Steroid with Neurotrophic Activity:  NGA0187

  摘要：

  A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6 alpha,7 beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.

  DOI：

  10.1021/jo051556d
• 作为产物：
  描述：

  (3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-5-Hydroxy-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-10-one 在 2,6-二甲基吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-10-eth-(Z)-ylidene-2,2,7a,9a-tetramethyl-8-triethylsilanyloxy-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthrene
  参考文献：
  名称：

  The Synthesis and Preliminary Biological Evaluation of a Novel Steroid with Neurotrophic Activity:  NGA0187

  摘要：

  A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6 alpha,7 beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.

  DOI：

  10.1021/jo051556d

文献信息

• The Synthesis and Preliminary Biological Evaluation of a Novel Steroid with Neurotrophic Activity:  NGA0187
  作者：Zihao Hua、David A. Carcache、Yuan Tian、Yue-Ming Li、Samuel J. Danishefsky

  DOI：10.1021/jo051556d

  日期：2005.11.1

  A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6 alpha,7 beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.