3α,7β,12α-triformyloxy-5β-cholan-24-oic acid | 166819-52-9

• 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,7β,12α-triformyloxy-5β-cholan-24-oic acid
• 英文别名: (4R)-4-[(3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-3,7,12-triformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 166819-52-9
• 化学式: C₂₇H₄₀O₈
• 分子量: 492.61
• InChiKey: OHJFKWAMNYLNEV-JPMHHYLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲酸 、 4-[(5S,7S,8S,10S,13R,17R)-3,7,12-三羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸 在 高氯酸 作用下， 反应 0.03h， 以98%的产率得到3α,7β,12α-triformyloxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Microwave-induced organic reactions of bile acids: Esterification, deformylation and deacetylation using mild reagents

  摘要：

  An efficient and convenient procedure for the esterification, deformylation, and deacetylation of bile acids is described. This is achieved by the addition of a catalytic amount of methanesulfonic acid or para-toluene sulfonic acid to a solution of bile acid in methanol in the domestic microwave oven. All these reactions were completed in the microwave oven within 1-3 min at 60% power (390 W) and the desired bile acids, namely trihydroxy-5 beta-cholestanoic acid, (23R)-3 alpha,7 alpha,23-trihydroxy-5 beta-cholan-24-oic acid, ursocholic acid and 7-ketolithocholic acid were isolated in 86-94% yield.

  DOI：

  10.1016/0039-128x(95)00004-a

文献信息

• Microwave-induced organic reactions of bile acids: Esterification, deformylation and deacetylation using mild reagents
  作者：B. Dayal、Keshava Rao、G. Salen

  DOI：10.1016/0039-128x(95)00004-a

  日期：1995.6

  An efficient and convenient procedure for the esterification, deformylation, and deacetylation of bile acids is described. This is achieved by the addition of a catalytic amount of methanesulfonic acid or para-toluene sulfonic acid to a solution of bile acid in methanol in the domestic microwave oven. All these reactions were completed in the microwave oven within 1-3 min at 60% power (390 W) and the desired bile acids, namely trihydroxy-5 beta-cholestanoic acid, (23R)-3 alpha,7 alpha,23-trihydroxy-5 beta-cholan-24-oic acid, ursocholic acid and 7-ketolithocholic acid were isolated in 86-94% yield.
• 7β-hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol
  作者：B. Dayal、N.H. Ertel、J. Padia、K.R. Rapole、G. Salen

  DOI：10.1016/s0039-128x(97)00007-x

  日期：1997.5

  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.