(6R,13R)-6-(tert-butyldimethylsilyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate | 1204770-38-6

• 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: (6R,13R)-6-(tert-butyldimethylsilyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate
• CAS: 1204770-38-6
• 化学式: C₂₆H₃₇F₃O₅SSi
• 分子量: 546.723
• InChiKey: DDZKGSAVBNDNLO-HWZJXXSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (6R,13R)-6-(tert-butyldimethylsilyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 六甲基二硅氮烷 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以93%的产率得到(6R,13R)-6-(tert-butyldimethylsilyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene-3-carboxamide
  参考文献：
  名称：

  Structure elucidation by synthesis of four metabolites of the antitumor drug ENMD-1198 detected in human plasma samples

  摘要：

  ENMD-1198 is a biologically active analogue of the antitumor drug 2-methoxyestradiol. Four human metabolites of ENMD-1198 were identified through synthesis and liquid chromatography/mass spectrometry comparisons of the metabolites with the synthetic standards. Two metabolites (3 and 4) are epimers resulting from benzylic hydroxylation at C-6. Two additional metabolites (5 and 6) are formed by epimeric hydroxylation at C-6 and alpha-epoxidation of the 16,17-alkene. The syntheses provided sufficient quantities of the metabolites for cytotoxicity studies to proceed. The 6-beta-ol 4 was moderately less cytotoxic than the parent drug, while the remaining three metabolites (3, 5, and 6) were significantly less cytotoxic. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.046
• 作为产物：
  描述：

  (6R,13S)-6-(tert-butyldimethylsilyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diyl bis(trifluoromethanesulfonate) 在 甲酸 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到(6R,13R)-6-(tert-butyldimethylsilyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Structure elucidation by synthesis of four metabolites of the antitumor drug ENMD-1198 detected in human plasma samples

  摘要：

  ENMD-1198 is a biologically active analogue of the antitumor drug 2-methoxyestradiol. Four human metabolites of ENMD-1198 were identified through synthesis and liquid chromatography/mass spectrometry comparisons of the metabolites with the synthetic standards. Two metabolites (3 and 4) are epimers resulting from benzylic hydroxylation at C-6. Two additional metabolites (5 and 6) are formed by epimeric hydroxylation at C-6 and alpha-epoxidation of the 16,17-alkene. The syntheses provided sufficient quantities of the metabolites for cytotoxicity studies to proceed. The 6-beta-ol 4 was moderately less cytotoxic than the parent drug, while the remaining three metabolites (3, 5, and 6) were significantly less cytotoxic. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.046