[(3S,8S,9S,10R,11S,13S,14S)-10,13-dimethyl-3-triethylsilyloxyspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-triethylsilane | 871247-47-1

• 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: [(3S,8S,9S,10R,11S,13S,14S)-10,13-dimethyl-3-triethylsilyloxyspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-triethylsilane
• CAS: 871247-47-1
• 化学式: C₃₃H₆₀O₄Si₂
• 分子量: 577.008
• InChiKey: XVARWSPYBXXVRW-MIAZNNDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.08
• 重原子数：
  39
• 可旋转键数：
  10
• 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：

  [(3S,8S,9S,10R,11S,13S,14S)-10,13-dimethyl-3-triethylsilyloxyspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-triethylsilane 在 吡啶 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 硼烷 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 (3S,5S,6R,7R,8S,9S,10S,11S,13S,14S)-3,6,7-Trihydroxy-10,13-dimethyl-11-triethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-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：

  三乙基硅基三氟甲磺酸酯 、 17,17-ethylenedioxy-androst-5-ene-3β,11β-diol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到[(3S,8S,9S,10R,11S,13S,14S)-10,13-dimethyl-3-triethylsilyloxyspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-triethylsilane
  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.