[(3S,8R,9S,10R,13S,14S,15S,16S,17E)-3-[tert-butyl(diphenyl)silyl]oxy-17-ethylidene-15-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl] acetate | 865441-04-9

• 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: [(3S,8R,9S,10R,13S,14S,15S,16S,17E)-3-[tert-butyl(diphenyl)silyl]oxy-17-ethylidene-15-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl] acetate
• CAS: 865441-04-9
• 化学式: C₃₉H₅₂O₄Si
• 分子量: 612.925
• InChiKey: KIGYGHFFNACMBG-JTCXTNLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3S,8R,9S,10R,13S,14S,15S,16S,17E)-3-[tert-butyl(diphenyl)silyl]oxy-17-ethylidene-15-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl] acetate 在 platinum on activated charcoal lithium aluminium tetrahydride 、 lutidine 、 氢气 作用下， 以 丙酸 为溶剂， 生成 (R)-3-[(3S,8R,9S,10R,13R,14S,15R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-15-triethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butyric acid ethyl ester
  参考文献：
  名称：

  Synthesis of xestobergsterol A from dehydroepiandrosterone

  摘要：

  Xestobergsterol A, a potent inhibitor of histamine release, has been synthesized from dehydroepiandrosterone in a route that used introduction of a novel 15-oxygen functionality, side-chain construction via the orthoester Claisen rearrangement and TBAF-promoted epimerization-aldol condensation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.042
• 作为产物：
  描述：

  (3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one 在 palladium diacetate titanium(IV) isopropylate 、 叔丁基过氧化氢 、 氧气 、 苄基三甲基氢氧化铵 、 双(三甲基硅烷基)氨基钾 、 lithium diisopropyl amide 作用下， 生成 [(3S,8R,9S,10R,13S,14S,15S,16S,17E)-3-[tert-butyl(diphenyl)silyl]oxy-17-ethylidene-15-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl] acetate
  参考文献：
  名称：

  Synthesis of xestobergsterol A from dehydroepiandrosterone

  摘要：

  Xestobergsterol A, a potent inhibitor of histamine release, has been synthesized from dehydroepiandrosterone in a route that used introduction of a novel 15-oxygen functionality, side-chain construction via the orthoester Claisen rearrangement and TBAF-promoted epimerization-aldol condensation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.042