methyl 3α-acetyloxy-7-oxo-12α-hydroxy-5β-cholan-24-oate | 21059-39-2

• 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: methyl 3α-acetyloxy-7-oxo-12α-hydroxy-5β-cholan-24-oate
• 英文别名: methyl 3α-acetoxy-12α-hydroxy-7-oxo-5β-cholan-24-oate；methyl 7-oxodeoxycholate 3-acetate；methyl 3α-acetoxy-12α-hydroxy-7-keto-5β-cholan-24-oate；3α-acetoxy-12α-hydroxy-7-oxo-5β-cholan-24-oic acid methyl ester；12α-Hydroxy-3α-acetoxy-7-oxo-5β-cholansaeure-(24)-methylester；3α-Acetoxy-12α-hydroxy-7-oxo-5β-cholan-24-saeure-methylester；methyl (4R)-4-[(3R,5S,8R,9S,10S,12S,13R,14S,17R)-3-acetyloxy-12-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 21059-39-2
• 化学式: C₂₇H₄₂O₆
• 分子量: 462.627
• InChiKey: IFEKJEZROGOZDU-RZNRKWMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3α-acetyloxy-7-oxo-12α-hydroxy-5β-cholan-24-oate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Asymmetric Induction by the Cholestanic Moiety on Tropos Species:  Synthesis and Stereochemical Characterization of Bile Acid-Based Biphenyl Phosphites

  摘要：

  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.

  DOI：

  10.1021/jo0606453
• 作为产物：
  描述：

  methyl cholate 3-acetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 以60%的产率得到methyl 3α-acetyloxy-7-oxo-12α-hydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Asymmetric Induction by the Cholestanic Moiety on Tropos Species:  Synthesis and Stereochemical Characterization of Bile Acid-Based Biphenyl Phosphites

  摘要：

  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.

  DOI：

  10.1021/jo0606453

文献信息

• 一种7-酮基石胆酸的合成方法
  申请人：华东师范大学

  公开号：CN107033208A

  公开（公告）日：2017-08-11

  本发明公开了一种奥贝胆酸的中间体7‑酮基石胆酸(3α‑羟基‑7‑酮‑5β‑胆甾烷‑24‑酸)的化学合成方法，属有机化学合成领域。该方法采用胆酸为原料，经过7α‑羟基的选择性氧化、侧链羧基的酯化、3α‑羟基的酯化、12α‑羟基的甲磺酸酯化，消除、加氢、水解等反应，合成所述奥贝胆酸的中间体7‑酮基石胆酸。本发明方法采用廉价的胆酸为原料，合成方法新颖、成本低、收率高、环境友好，便于工业化生产。
• 一种鹅去氧胆酸的合成方法
  申请人：华东师范大学

  公开号：CN107383137A

  公开（公告）日：2017-11-24

  本发明公开了一种鹅去氧胆酸的合成方法，采用胆酸为原料，经过7α‑羟基选择性氧化、侧链羧基酯化、3α‑羟基酯化、12α‑羟基甲磺酸酯化、消除、水解、还原等反应制备鹅去氧胆酸。本发明鹅去氧胆酸的合成方法，步骤简单，副反应少，收率高，原料易得，适用于工业化生产，解决了现有技术中合成成本高、收率低等问题，适于工业化大规模生产。
• 一种熊去氧胆酸的合成方法
  申请人：华东师范大学

  公开号：CN107417757B

  公开（公告）日：2020-12-22

  本发明公开了一种熊去氧胆酸的合成方法，采用胆酸为原料，经过7α‑羟基选择性氧化、侧链羧基酯化、3α‑羟基酯化、12α‑羟基甲磺酸酯化、消除、水解、还原等步骤合成熊去氧胆酸。本发明熊去氧胆酸的合成方法，步骤简单，副反应少，收率高，原料易得，适用于工业化生产，解决了现有技术中合成成本高、收率低等问题，具有广泛的应用前景。
• A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid
  作者：Xiao-Long He、Li-Ting Wang、Xiang-Zhong Gu、Jie-Xin Xiao、Wen-Wei Qiu

  DOI：10.1016/j.steroids.2018.10.009

  日期：2018.12

  A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation

  通过廉价和易于获得的胆酸的多次反应，开发了生产熊去氧胆酸（UDCA）和奥贝胆酸（OCA）的新型合成途径。还研究和优化了甲磺酸酯基关键消除反应的反应条件，包括溶剂，碱和反应温度。在制备UDCA和OCA的简单合成路线中，大多数反应步骤均具有较高的转化率，平均收率可达胆甾醇的65％（7个步骤）和36％（11个步骤），最高可达94％和92％。酸。这一有前途的路线为潜在的大规模生产UDCA和OCA提供了经济有效的策略。
• Synthesis of disulfates of unconjugated and conjugated bile acids.
  作者：JUNICHI GOTO、YOSHIHISA SANO、TOSHIYUKI CHIKAI、TOSHIO NAMBARA

  DOI：10.1248/cpb.35.4562

  日期：——

  The disulfates of unconjugated, and glycine- and taurine-conjugated bile acids have been synthesized. Cholic acid derivatives appropriately protected were sulfated with sulfur trioxide-triethylamine complex in pyridine in the usual manner. Subsequent hydrolysis and/or sodium borohydride reduction provided the desired disulfates of cholates in satisfactory yields. Dihydroxylated bile acid disulfates were also prepared. The nuclear magnetic resonance spectral data for bile acid disulfates and related compounds are tabulated.

  已合成未结合的以及甘氨酸和牛磺酸结合的胆汁酸的二硫酸盐。适当保护的胆酸衍生物在吡啶中采用三氧化硫-三乙胺络合物进行磺酸化，方法如常。随后水解和/或氢化钠还原提供了理想的胆酸二硫酸盐，收率令人满意。同时也制备了二羟基胆汁酸的二硫酸盐。胆汁酸二硫酸盐及相关化合物的核磁共振光谱数据已列出。