(3S,5S,8S,9R,10R,13R,14R,17R)-19-((tert-butoxycarbonyl)-L-leucyl)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-8,5-(epoxyimino)cyclopenta[a]phenanthren-3-yl acetate | 1167539-94-7

• 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,5S,8S,9R,10R,13R,14R,17R)-19-((tert-butoxycarbonyl)-L-leucyl)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-8,5-(epoxyimino)cyclopenta[a]phenanthren-3-yl acetate
• CAS: 1167539-94-7
• 化学式: C₄₁H₆₆N₂O₆
• 分子量: 682.985
• InChiKey: QRAFWAJZGKINFN-VEUVDSABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,5S,8S,9R,10R,13R,14R,17R)-19-((tert-butoxycarbonyl)-L-leucyl)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-8,5-(epoxyimino)cyclopenta[a]phenanthren-3-yl acetate 在 potassium carbonate 、 水 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以87%的产率得到tert-butyl N-[(2S)-1-[(1S,2R,5R,6R,9R,10R,13S,15S)-5-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-13-hydroxy-6,10-dimethyl-17-oxa-16-azapentacyclo[13.2.2.01,9.02,6.010,15]nonadec-18-en-16-yl]-4-methyl-1-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol

  摘要：

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.

  DOI：

  10.1021/ol900997t
• 作为产物：
  描述：

  (3b,22E)-麦角甾-5,7,22-三烯-3b-醇 3-乙酸酯 、 (S)-Nα-(tert-butoxycarbonyl)leucine hydroxamic acid 在 四丁基高碘酸铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以93%的产率得到(3S,5S,8S,9R,10R,13R,14R,17R)-19-((tert-butoxycarbonyl)-L-leucyl)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-8,5-(epoxyimino)cyclopenta[a]phenanthren-3-yl acetate
  参考文献：
  名称：

  Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol

  摘要：

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.

  DOI：

  10.1021/ol900997t