[(3'S,5'S,6'R,8'S,9'S,10'S,11'S,13'S,14'S)-3',11'-bis[[tert-butyl(dimethyl)silyl]oxy]-10',13'-dimethyl-7'-oxospiro[1,3-dioxolane-2,17'-2,3,4,5,6,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-6'-yl] benzoate | 871247-34-6

• 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: [(3'S,5'S,6'R,8'S,9'S,10'S,11'S,13'S,14'S)-3',11'-bis[[tert-butyl(dimethyl)silyl]oxy]-10',13'-dimethyl-7'-oxospiro[1,3-dioxolane-2,17'-2,3,4,5,6,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-6'-yl] benzoate
• CAS: 871247-34-6
• 化学式: C₄₀H₆₄O₇Si₂
• 分子量: 713.115
• InChiKey: TUAQNIFWCRKZTF-RLLHQQNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.18
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(3'S,5'S,6'R,8'S,9'S,10'S,11'S,13'S,14'S)-3',11'-bis[[tert-butyl(dimethyl)silyl]oxy]-10',13'-dimethyl-7'-oxospiro[1,3-dioxolane-2,17'-2,3,4,5,6,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-6'-yl] benzoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 (3'S,5'S,6'R,8'S,9'S,10'S,11'S,13'S,14'S)-3',11'-bis[[tert-butyl(dimethyl)silyl]oxy]-6'-hydroxy-10',13'-dimethylspiro[1,3-dioxolane-2,17'-2,3,4,5,6,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-7'-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：

  17,17-ethylenedioxy-androst-5-ene-3β,11β-diol 在 2,6-二甲基吡啶 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 硼烷四氢呋喃络合物 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 43.5h， 生成 [(3'S,5'S,6'R,8'S,9'S,10'S,11'S,13'S,14'S)-3',11'-bis[[tert-butyl(dimethyl)silyl]oxy]-10',13'-dimethyl-7'-oxospiro[1,3-dioxolane-2,17'-2,3,4,5,6,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-6'-yl] benzoate
  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.