(2R,4R)-2-((3S,8R,9S,10R,13R,14S,15R,17R)-15-(benzoyloxy)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptan-4-yl benzoate | 865441-18-5

• 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: (2R,4R)-2-((3S,8R,9S,10R,13R,14S,15R,17R)-15-(benzoyloxy)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptan-4-yl benzoate
• CAS: 865441-18-5
• 化学式: C₅₇H₇₀O₆Si
• 分子量: 879.265
• InChiKey: NNAKAJPGWAYRHP-NBPBJIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.82
• 重原子数：
  64.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-((3S,8R,9S,10R,13R,14S,15R,17R)-15-(benzoyloxy)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptan-4-yl benzoate 在 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 硼烷四氢呋喃络合物 、 双氧水 、 phosphorus pentoxide 作用下， 生成 [(1R,2R,6R,7S,9S,12R,13S,16R,17R,19R,20S)-17-[(2R,4R)-4-benzoyloxy-6-methylheptan-2-yl]-9-[tert-butyl(diphenyl)silyl]oxy-12,16-dimethyl-3,5-dioxapentacyclo[11.7.0.02,6.07,12.016,20]icosan-19-yl] benzoate
  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,8R,9S,10R,13R,14S,15R,17R)-17-[(2R,4R)-4-benzoyloxy-6-methylheptan-2-yl]-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-15-yl] benzoate 在 N-羟基邻苯二甲酰亚胺 氧气 、 过氧化苯甲酰 、 copper dichloride 作用下， 以 吡啶 为溶剂， 以75%的产率得到(2R,4R)-2-((3S,8R,9S,10R,13R,14S,15R,17R)-15-(benzoyloxy)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptan-4-yl benzoate
  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