3α.7α.12α-triformyloxy-24-diazomethyl-5β-cholanone-(24) | 59457-89-5

• 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: 3α.7α.12α-triformyloxy-24-diazomethyl-5β-cholanone-(24)
• 英文别名: 3α.7α.12α-Triformyloxy-24-diazomethyl-5β-cholanon-(24)
• CAS: 59457-89-5
• 化学式: C₂₈H₄₀N₂O₇
• 分子量: 516.635
• InChiKey: VVKGNGKQFIJAOY-NDJPRTQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  132.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3α.7α.12α-triformyloxy-24-diazomethyl-5β-cholanone-(24) 在 silver nitrate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 cholic acid
  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：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 作用下， 生成 3α.7α.12α-triformyloxy-24-diazomethyl-5β-cholanone-(24)
  参考文献：
  名称：

  类固醇和性激素。（第91部分）。关于β'-[3α，7α，12β-三氧基-去甲胆烷基-（23）]-Δα '， β'-丁烯内酯，洋地黄苷配体的同系物

  摘要：

  DOI：

  10.1002/hlca.19440270120

文献信息

• A facile synthesis of 5?-cholestane-3?, 7?, 12?,25-tetrol*1
  作者：B DAYAL

  DOI：10.1016/0039-128x(80)90144-0

  日期：1980.4

  A convenient procedure for the synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol via a modified homologation sequence of the intermediate 3 alpha,7 alpha,12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane involving a homogeneous medium is described. This involves treating the intermediate alpha-diazoketone in methanol with a solution of silver benzoate in triethylamine. Grignard reaction of the resulting triformyloxy methyl homocholate yielded 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol. Large amounts of this bile alcohol were needed to further investigate the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX).