22-(4-benzoylbenzoyloxy)-3β-(tert-butyldimethylsilyloxy)-14-trimethylsilyloxy-5β,14β-card-20(22)-enolide | 332949-17-4

• 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: 22-(4-benzoylbenzoyloxy)-3β-(tert-butyldimethylsilyloxy)-14-trimethylsilyloxy-5β,14β-card-20(22)-enolide
• 英文别名: [3-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-14-trimethylsilyloxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-5-oxo-2H-furan-4-yl] 4-benzoylbenzoate
• CAS: 332949-17-4
• 化学式: C₄₆H₆₄O₇Si₂
• 分子量: 785.181
• InChiKey: GOYOQIRGRGVDIR-PAZWGSHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.91
• 重原子数：
  55
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  22-(4-benzoylbenzoyloxy)-3β-(tert-butyldimethylsilyloxy)-14-trimethylsilyloxy-5β,14β-card-20(22)-enolide 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 77.0h， 生成 22-(4-benzoylbenzoyloxy)-14-hydroxy-3β-(4-isothiocyanatobenzoyloxy)-5β,14β-card-20(22)-enolide
  参考文献：
  名称：

  A Novel Cardenolide Photoaffinity Label for the Na/K-ATPase

  摘要：

  A benzoylbenzoyloxy derivative of digitoxigenin has been prepared which is the first cardenolide with an affinity label in the lactone ring. It inhibits the Na+/K+-ATPase almost as effectively as digitoxigenin itself. The activity was lost when in addition a biotin tag was attached to ring A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00916-9
• 作为产物：
  描述：

  4-苯甲酰苯甲酸 、 4-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-3-hydroxy-5H-furan-2-one 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到22-(4-benzoylbenzoyloxy)-3β-(tert-butyldimethylsilyloxy)-14-trimethylsilyloxy-5β,14β-card-20(22)-enolide
  参考文献：
  名称：

  A Novel Cardenolide Photoaffinity Label for the Na/K-ATPase

  摘要：

  A benzoylbenzoyloxy derivative of digitoxigenin has been prepared which is the first cardenolide with an affinity label in the lactone ring. It inhibits the Na+/K+-ATPase almost as effectively as digitoxigenin itself. The activity was lost when in addition a biotin tag was attached to ring A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00916-9