3-O-<5-O-(p-tolylsulfonyl)-β-D-ribofuranosyl>digitoxigenin | 99604-85-0

• 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: 3-O-<5-O-(p-tolylsulfonyl)-β-D-ribofuranosyl>digitoxigenin
• CAS: 99604-85-0
• 化学式: C₃₅H₄₈O₁₀S
• 分子量: 660.826
• InChiKey: KHHJTSSHMIMROR-WGLAXOCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  46.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  148.82
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-O-<5-O-(p-tolylsulfonyl)-β-D-ribofuranosyl>digitoxigenin 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以93%的产率得到3-O-(5-azido-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：

  2,3,5-tri-O-acetyl-D-ribofuranosyl bromide 在 吡啶 、 氨 、 氰化汞 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 25.75h， 生成 3-O-<5-O-(p-tolylsulfonyl)-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