14,20β-dihydroxy-5β,14β-pregnan-3β-yl acetate | 83059-72-7

• 英文名称: 14,20β-dihydroxy-5β,14β-pregnan-3β-yl acetate
• 英文别名: 5β-pregnane-3β,14β,20β-triol 3-acetate；3β-acetoxy-14,20β-dihydroxy-5β,14β-pregnane；3β-acetoxy-14,20(R)-dihydroxy-5β,14β-pregnane；[(3S,5R,8R,9S,10S,13R,14S,17S)-14-hydroxy-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 83059-72-7
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: WXPLTPNJECKYBN-OAXJHHGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  14,20β-dihydroxy-5β,14β-pregnan-3β-yl acetate 在 四氯化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以15 mg的产率得到20β-hydroxy-5β-pregn-14-en-3β-yl acetate
  参考文献：
  名称：

  Templeton, John F.; Ling, Yangzhi; Zeglam, Talal H., Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2503 - 2518

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-Acetoxy-14-hydroxy-5β,14β-pregnan-20-on 在 lithium tri(t-butoxy)aluminum hydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以420 mg的产率得到14,20β-dihydroxy-5β,14β-pregnan-3β-yl acetate
  参考文献：
  名称：

  Cardiac glycoside-like structure and function of 5.beta.,14.beta.-pregnanes

  摘要：

  5 beta-Reduction and 14 beta-substitution convert the planar progesterone molecule to the cardiac glycoside configuration--A and D rings of the steroid moiety are bent toward the alpha-face relative to the B and C rings. Potency of the 5 beta,14 beta-derivative in a [3H]ouabain binding assay or its ability to inhibit the sodium pump in red blood cells is enhanced by 3 beta-hydroxylation, 20 beta-hydroxylation, and 3 beta-glycosidation. Synthesis of 14,20 beta-dihydroxy-3 beta-(beta-D-glucopyranosyloxy)- 5 beta,14 beta-pregnane from digitoxin is described. The glucoside is 1/20 as potent as ouabain and elicits prominent, sustained, positive inotropy in isolated cardiac muscle.

  DOI：

  10.1021/jm00128a047