(R)-5-((3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-hexanoic acid methyl ester | 191352-70-2

• 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: (R)-5-((3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-hexanoic acid methyl ester
• CAS: 191352-70-2
• 化学式: C₂₆H₄₄O₅
• 分子量: 436.632
• InChiKey: LEHTYSFVJCGXTB-FREJXKSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 (R)-5-((3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-hexanoic acid methyl ester 以 乙醚 、 苯 为溶剂， 以5%的产率得到(3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-17-((R)-4-Hydroxy-1,4-dimethyl-pentyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol
  参考文献：
  名称：

  7β-hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol

  摘要：

  A rapid and easily performed procedure for the synthesis of 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol by means of an efficient homologation sequence of the intermediate, 3 alpha, 7 beta, 12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane is described. The reaction sequence involved treating the intermediate, alpha-diazoketone in methanol with 3% AgNO3 or Ag2O, anhydrous Na2CO3, Na2S2O3/H2O resulting in the formation of homoursocholic acid in high yield. Esterification of the homoursocholic acid in methanol containing a catalytic amount of methanesulfonic acid under microwave irradiation conditions gave methyl homoursocholate. The subsequent treatment of methyl homoursocholate with methyl magnesium iodide provided 5 beta-cholestane-3 alpha,7 beta,12 alpha,25-tetrol in 88% yield The products and synthetic intermediates prepared in these studies were fully characterized by the results of 1D and 2D NMR, and high-resolution mass spectral studies. These studies will help in further investigation of the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX) as well as other inborn errors of bile acid metabolism. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00007-x
• 作为产物：
  描述：

  3α,7β,12α-triformyloxy-5β-cholan-24-oic acid 在 草酰氯 、 甲烷磺酸 、 silver nitrate 作用下， 以 甲醇 为溶剂， 反应 6.01h， 生成 (R)-5-((3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-hexanoic acid methyl ester
  参考文献：
  名称：

  7β-hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol

  摘要：

  A rapid and easily performed procedure for the synthesis of 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol by means of an efficient homologation sequence of the intermediate, 3 alpha, 7 beta, 12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane is described. The reaction sequence involved treating the intermediate, alpha-diazoketone in methanol with 3% AgNO3 or Ag2O, anhydrous Na2CO3, Na2S2O3/H2O resulting in the formation of homoursocholic acid in high yield. Esterification of the homoursocholic acid in methanol containing a catalytic amount of methanesulfonic acid under microwave irradiation conditions gave methyl homoursocholate. The subsequent treatment of methyl homoursocholate with methyl magnesium iodide provided 5 beta-cholestane-3 alpha,7 beta,12 alpha,25-tetrol in 88% yield The products and synthetic intermediates prepared in these studies were fully characterized by the results of 1D and 2D NMR, and high-resolution mass spectral studies. These studies will help in further investigation of the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX) as well as other inborn errors of bile acid metabolism. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00007-x