3β-(α-L-rhamnopyranosyl)oxy-21-nor-5β-pregnane-1β,5,11α,14β,19-pentol-20-carboxylic acid | 162369-06-4

• 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: 3β-(α-L-rhamnopyranosyl)oxy-21-nor-5β-pregnane-1β,5,11α,14β,19-pentol-20-carboxylic acid
• 英文别名: (1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
• CAS: 162369-06-4
• 化学式: C₂₆H₄₂O₁₂
• 分子量: 546.612
• InChiKey: JTZISHAGMRDWDY-DLSQPTQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  218
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3β-(α-L-rhamnopyranosyl)oxy-21-nor-5β-pregnane-1β,5,11α,14β,19-pentol-20-carboxylic acid 以 甲醇 为溶剂， 以72 mg的产率得到3β-(α-L-rhamnopyranosyl)oxy-21-nor-5β-pregnane-1β,5,11α,14β,19-pentol-20-carboxylic acid methyl ester
  参考文献：
  名称：

  Pregnane and 21-norpregnane derivatives of ouabain that bind to the digitalis receptor

  摘要：

  14 beta-Hydroxy-5 beta-pregnane and 14 beta-hydroxy-21-nor-5 beta-pregnane derivatives of ouabain were synthesised and their structures established by NMR measurements. Binding affinity in an [H-3]ouabain radioligand binding assay was determined. Pregnane derivatives of ouabain are more polar than pregnane rhamnoside derivatives of digitoxigenin. Whereas ouabain binds similarly to digitoxigenin rhamnoside, the pregnane derivatives of ouabain have significantly weaker binding affinity than their congeners from digitoxigenin.

  DOI：

  10.1016/0223-5234(94)90140-6
• 作为产物：
  描述：

  ouabain 1,2',3',4',11,19-hexaacetate 在 sodium hydroxide 、 sodium periodate 、 potassium hydrogencarbonate 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 9.0h， 生成 3β-(α-L-rhamnopyranosyl)oxy-21-nor-5β-pregnane-1β,5,11α,14β,19-pentol-20-carboxylic acid
  参考文献：
  名称：

  Pregnane and 21-norpregnane derivatives of ouabain that bind to the digitalis receptor

  摘要：

  14 beta-Hydroxy-5 beta-pregnane and 14 beta-hydroxy-21-nor-5 beta-pregnane derivatives of ouabain were synthesised and their structures established by NMR measurements. Binding affinity in an [H-3]ouabain radioligand binding assay was determined. Pregnane derivatives of ouabain are more polar than pregnane rhamnoside derivatives of digitoxigenin. Whereas ouabain binds similarly to digitoxigenin rhamnoside, the pregnane derivatives of ouabain have significantly weaker binding affinity than their congeners from digitoxigenin.

  DOI：

  10.1016/0223-5234(94)90140-6