(3α,5β,12α)-12-(benzoyloxy)-3-hydroxycholan-24-oic acid methyl ester | 473462-06-5

• 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,5β,12α)-12-(benzoyloxy)-3-hydroxycholan-24-oic acid methyl ester
• 英文别名: methyl 3α-hydroxy-12α-benzoyloxy-5β-cholan-24-oate；[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-hydroxy-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-12-yl] benzoate
• CAS: 473462-06-5
• 化学式: C₃₂H₄₆O₅
• 分子量: 510.714
• InChiKey: GKYIHOAENSNFBX-PDORAURZSA-N

物化性质

• 沸点：
  589.3±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3α,5β,12α)-12-(benzoyloxy)-3-hydroxycholan-24-oic acid methyl ester 在 jones reagent 作用下， 以 丙酮 为溶剂， 以33.6 g的产率得到(5β,12α)-12-(benzoyloxy)-3-oxocholan-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
• 作为产物：
  描述：

  去氧胆酸 在 吡啶 、 sodium 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 (3α,5β,12α)-12-(benzoyloxy)-3-hydroxycholan-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

• Application of deoxycholic acid-based copper–phosphite complexes as ligands in the enantioselective conjugate addition of diethylzinc to acyclic enones
  作者：Anna Iuliano、Patrizia Scafato

  DOI：10.1016/s0957-4166(03)00044-2

  日期：2003.3

  Four phosphites obtained by linking enantiomerically pure binaphthylchlorophosphite to the two different hydroxy groups of deoxycholic acid were synthesized and used as chiral ligands in the enantioselective copper-catalyzed 1,4-addition of diethylzinc to acyclic enones. The ligands were screened for activity and enantioselectivity using chalcone as the substrate to establish the influence of the absolute configuration of the binaphthyl moiety as well as the position on the cholestanic backbone of the phosphite moiety. The ligand affording the best results was eventually used in the copper-catalyzed 1,4-addition to various acyclic enones, affording the alkylation products in good yields and e.e.s up to 78%. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Asymmetric Induction by the Cholestanic Moiety on <i>T</i><i>ropos</i> Species:  Synthesis and Stereochemical Characterization of Bile Acid-Based Biphenyl Phosphites
  作者：A. Iuliano、S. Facchetti、G. Uccello-Barretta

  DOI：10.1021/jo0606453

  日期：2006.6.1

  Three different bile acid-derived biphenyl phosphites were synthesized, starting from cholic and deoxycholic acids and biphenol, and their stereochemical features were checked by CD and NMR spectroscopies. On the basis of the spectroscopic results, the capability of the cholestanic system to induce a prevalent sense of twist on the biphenyl moiety of the bile acid-derived phosphites as well as their tropos nature was inferred.