1-(tert-Butyl-diphenyl-silanyloxy)-3-[(3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-propan-2-ol | 888954-92-5

• 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: 1-(tert-Butyl-diphenyl-silanyloxy)-3-[(3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-propan-2-ol
• CAS: 888954-92-5
• 化学式: C₄₆H₇₂O₃Si
• 分子量: 701.161
• InChiKey: QIXJAWXNLYZRRV-CJDGVAFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.43
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(tert-Butyl-diphenyl-silanyloxy)-3-[(3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-propan-2-ol 在 四丁基氟化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 生成 2-(benzyloxy)-3-(((3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel steroid-modified ether phospholipids

  摘要：

  Platelet activating factor is one of the most potent inflammatory ether phospholipid mediators known and structurally modified analogues are of considerable interest as potential therapeutic preparations. Inspired by the proposed structure for a novel endogenous hydroxy-PAF analogue isolated recently from gingival crevicular fluid, we designed and prepared two novel steroid-modified ether phospholipids. These two novel compounds exhibit marked chemical and biological similarities to their endogenous prototype and they antagonize it being less active in inducing washed platelet aggregation through PAF receptors. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.07.007
• 作为产物：
  描述：

  5α（H）-Cholestan-3α醇 、 tert-butyl(oxiran-2-ylmethoxy)diphenylsilane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到1-(tert-Butyl-diphenyl-silanyloxy)-3-[(3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-propan-2-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel steroid-modified ether phospholipids

  摘要：

  Platelet activating factor is one of the most potent inflammatory ether phospholipid mediators known and structurally modified analogues are of considerable interest as potential therapeutic preparations. Inspired by the proposed structure for a novel endogenous hydroxy-PAF analogue isolated recently from gingival crevicular fluid, we designed and prepared two novel steroid-modified ether phospholipids. These two novel compounds exhibit marked chemical and biological similarities to their endogenous prototype and they antagonize it being less active in inducing washed platelet aggregation through PAF receptors. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.07.007