4-(3-((5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one | 99604-87-2

• 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: 4-(3-((5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
• 英文别名: 3-O-(5-amino-5-deoxy-β-D-ribofuranosyl)digitoxigenin
• CAS: 99604-87-2
• 化学式: C₂₈H₄₃NO₇
• 分子量: 505.652
• InChiKey: SBGOTKKQCANQOM-NHATUGJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  131.47
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-(3-((5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one 在 吡啶 作用下， 反应 3.5h， 以70%的产率得到3-O-(5-acetamido-2,3-diO-acetyl-5-deoxy-β-D-ribofuranosyl)digitoxigenin
  参考文献：
  名称：

  Digitoxigenin 3-O-.beta.-D-furanosides

  摘要：

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.

  DOI：

  10.1021/jm00152a012
• 作为产物：
  描述：

  2-(acetoxymethyl)-5-((14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydrofuran-3,4-diyl diacetate 在 镍 吡啶 、 叠氮化锂 、 氨 、 氢气 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 31.25h， 生成 4-(3-((5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
  参考文献：
  名称：

  Digitoxigenin 3-O-.beta.-D-furanosides

  摘要：

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.

  DOI：

  10.1021/jm00152a012