Acetic acid (3S,5S,7R,8S,9S,10R,11S,13S,14S,16S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-10,13-dimethyl-6-oxo-11-triethylsilanyloxy-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester | 871247-75-5

• 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: Acetic acid (3S,5S,7R,8S,9S,10R,11S,13S,14S,16S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-10,13-dimethyl-6-oxo-11-triethylsilanyloxy-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester
• 英文别名: [(3S,5S,7R,8S,9S,10R,11S,13S,14S,16S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7-hydroxy-10,13-dimethyl-6-oxo-11-triethylsilyloxy-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
• CAS: 871247-75-5
• 化学式: C₄₂H₇₆O₆Si₂
• 分子量: 733.233
• InChiKey: IFJQOWUPMMZCJR-NKRKNDHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.21
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,5S,7R,8S,9S,10R,11S,13S,14S,16S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-10,13-dimethyl-6-oxo-11-triethylsilanyloxy-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 5.5h， 以4.2 mg的产率得到anicequol
  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：

  (3S,5S,6R,7R,8S,9S,10S,11S,13S,14S)-10,13-dimethyl-3,11-bis(triethylsilyloxy)spiro[1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-6,7-diol 在 吡啶 、 2,6-二甲基吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 potassium tert-butylate 、 叔丁基锂 、 copper(l) cyanide 、 戴斯-马丁氧化剂 、 1,2-乙二硫醇 、 溶剂黄146 、 (+)-10-camphorsulfonic acid 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 29.5h， 生成 Acetic acid (3S,5S,7R,8S,9S,10R,11S,13S,14S,16S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-10,13-dimethyl-6-oxo-11-triethylsilanyloxy-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester
  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