(3α,5β,12α)-3,12-bis(benzoyloxy)-cholan-24-oic acid methyl ester | 60918-27-6

• 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,5β,12α)-3,12-bis(benzoyloxy)-cholan-24-oic acid methyl ester
• 英文别名: 3α,12α-dibenzoyloxy-5β-cholanoic acid-(24)-methyl ester；3α,12α-Dibenzoyloxy-5β-cholansaeure-(24)-methylester；5beta-Cholanic acid-3alpha,12alpha-diol dibenzoate methyl ester；[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-12-benzoyloxy-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 60918-27-6
• 化学式: C₃₉H₅₀O₆
• 分子量: 614.822
• InChiKey: KFUKAOONKVKBGZ-KBQFLLFUSA-N

物化性质

• 沸点：
  663.3±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3α,5β,12α)-3,12-bis(benzoyloxy)-cholan-24-oic acid methyl ester 在 jones reagent 、 溴 、 sodium 、 lithium carbonate 、 溶剂黄146 、 lithium bromide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.67h， 生成 (12α)-12-(benzoyloxy)-3-oxochol-4-en-24-oic acid
  参考文献：
  名称：

  Synthesis of [3,4-¹³C₂]-Enriched Bile Salts as NMR Probes of Protein−Ligand Interactions

  摘要：

  Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-C-13(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-C-13(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-C-13(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)- double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-C-13(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and H-1-C-13 HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.

  DOI：

  10.1021/jo0259109
• 作为产物：
  描述：

  去氧胆酸 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 (3α,5β,12α)-3,12-bis(benzoyloxy)-cholan-24-oic acid methyl ester
  参考文献：
  名称：

  Synthesis of [3,4-¹³C₂]-Enriched Bile Salts as NMR Probes of Protein−Ligand Interactions

  摘要：

  Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-C-13(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-C-13(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-C-13(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)- double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-C-13(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and H-1-C-13 HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.

  DOI：

  10.1021/jo0259109

文献信息

• Seroflocculating Steroids. IV.¹ Unsaturated Bile Acid Esters²
  作者：Frederic C. Chang、Aaron Feldstein、Jane Ransom Gray、George S. McCaleb、Douglas H. Sprunt

  DOI：10.1021/ja01566a039

  日期：1957.5
• The Preparation and Degradation of Lithocholic Acid
  作者：Willard M. Hoehn、Harold L. Mason

  DOI：10.1021/ja01860a036

  日期：1940.3
• McKenzie; McGuckin; Kendall, Journal of Biological Chemistry, 1946, vol. 162, p. 555,558, 562
  作者：McKenzie、McGuckin、Kendall

  DOI：——

  日期：——
• Synthesis of [3,4-¹³C₂]-Enriched Bile Salts as NMR Probes of Protein−Ligand Interactions
  作者：Gregory P. Tochtrop、Gregory T. DeKoster、David P. Cistola、Douglas F. Covey

  DOI：10.1021/jo0259109

  日期：2002.9.1

  Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-C-13(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-C-13(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-C-13(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)- double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-C-13(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and H-1-C-13 HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.