[(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 | 865441-12-9

• 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: [(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
• CAS: 865441-12-9
• 化学式: C₅₈H₇₄O₇Si
• 分子量: 911.307
• InChiKey: QEXQPDCNFKTYJR-ZMDWVFPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.69
• 重原子数：
  66
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  [(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 在 lithium aluminium tetrahydride 、 lutidine 、 四丁基氟化铵 、 L-Selectride 、 戴斯-马丁氧化剂 作用下， 生成 (3aR,3bS,5R,7aR,7bS,9aR,10R,12aS,12bR,12cR)-5-(tert-Butyl-dimethyl-silanyloxy)-10-((R)-1,5-dimethyl-3-oxo-hexyl)-7a,9a-dimethyl-hexadecahydro-1,3-dioxa-dicyclopenta[a,l]phenanthren-12-one
  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：

  (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