3-oxo-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β) | 668989-83-1

• 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: 3-oxo-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β)
• 英文别名: methyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 668989-83-1
• 化学式: C₄₉H₇₈O₅
• 分子量: 747.155
• InChiKey: NORXCYNATQOKBL-PNEPYLKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-oxo-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β) 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到3α-hydroxy-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β)
  参考文献：
  名称：

  Synthesis of ester-linked lithocholic acid dimers

  摘要：

  Four lithocholic acid dimers were synthesised via esterification. The ester-linked dimer, 3-oxo-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), was obtained by condensation of methyl lithocholate with 3-oxo-5beta-cholan-24-oic acid. Borohydride reduction of this ester-linked dimer gave 3alpha-hydroxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), which was acetylated to 3alpha-acetoxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta). Reaction of methyl lithocholate with oxalyl chloride yielded the oxalate dimer, bis(5beta-cholan-24-oic acid methyl ester)-3alpha-yl oxalate. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2003.08.015
• 作为产物：
  描述：

  石胆酸 在 4-二甲氨基吡啶 、 jones' reagent 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 72.5h， 生成 3-oxo-5β-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3α,5β)
  参考文献：
  名称：

  Synthesis of ester-linked lithocholic acid dimers

  摘要：

  Four lithocholic acid dimers were synthesised via esterification. The ester-linked dimer, 3-oxo-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), was obtained by condensation of methyl lithocholate with 3-oxo-5beta-cholan-24-oic acid. Borohydride reduction of this ester-linked dimer gave 3alpha-hydroxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), which was acetylated to 3alpha-acetoxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta). Reaction of methyl lithocholate with oxalyl chloride yielded the oxalate dimer, bis(5beta-cholan-24-oic acid methyl ester)-3alpha-yl oxalate. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2003.08.015

文献信息

• Synthesis of ester-linked lithocholic acid dimers
  作者：Lutfun Nahar、Alan B Turner

  DOI：10.1016/j.steroids.2003.08.015

  日期：2003.12

  Four lithocholic acid dimers were synthesised via esterification. The ester-linked dimer, 3-oxo-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), was obtained by condensation of methyl lithocholate with 3-oxo-5beta-cholan-24-oic acid. Borohydride reduction of this ester-linked dimer gave 3alpha-hydroxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), which was acetylated to 3alpha-acetoxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta). Reaction of methyl lithocholate with oxalyl chloride yielded the oxalate dimer, bis(5beta-cholan-24-oic acid methyl ester)-3alpha-yl oxalate. (C) 2003 Elsevier Inc. All rights reserved.