(3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2,2,7a,9a-tetramethyl-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-10-one | 871247-37-9

• 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)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2,2,7a,9a-tetramethyl-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-10-one
• 英文别名: (1S,2R,6R,7S,9S,12S,13S,14S,16S,20S)-14-[tert-butyl(dimethyl)silyl]oxy-9-hydroxy-4,4,12,16-tetramethyl-3,5-dioxapentacyclo[11.7.0.02,6.07,12.016,20]icosan-17-one
• CAS: 871247-37-9
• 化学式: C₂₈H₄₈O₅Si
• 分子量: 492.772
• InChiKey: ICWJWANAPHNKEV-SFVKYTKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2,2,7a,9a-tetramethyl-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-10-one 在 吡啶 、 2,6-二甲基吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 potassium tert-butylate 、 叔丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 9.5h， 生成 Acetic acid (3S,5S,6R,7R,8S,9S,10S,11S,13S,14S,16S,17R)-11-(tert-butyl-dimethyl-silanyloxy)-3,6,7-trihydroxy-10,13-dimethyl-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
• 作为产物：
  描述：

  tert-butyl-[(3S,8S,9S,10R,11S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-11-yl]oxy-dimethylsilane 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 硼烷四氢呋喃络合物 、 camphor-10-sulfonic acid 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.5h， 生成 (3aR,3bS,5S,7aS,7bS,8S,9aS,12aS,12bS,12cR)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2,2,7a,9a-tetramethyl-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-10-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