(R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid | 145476-20-6

• 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: (R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid
• 英文别名: 3a-Tetrahydropyranyloxy-5b-cholan-24-oic acid；(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 145476-20-6
• 化学式: C₂₉H₄₈O₄
• 分子量: 460.698
• InChiKey: CWMSOXIPRFRNIU-YCEAHBPSSA-N

物化性质

• 沸点：
  572.2±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3α-tetrahydropyranyloxy-chol-24-ol
  参考文献：
  名称：

  Syntheses of potential spin probes for biomembranes - tempo and proxyl nitroxides of lithocholic acid

  摘要：

  The synthesis of a steroidal spin label 10 containing a tempo nitroxide group in the side chain of lithocholic acid 1 is reported. This is the first report of a tempo nitroxide in d steroidal side chain. The methodology involved d Wittig condensation between the steroidal phosphonium ylide 7 and tempone 9. The synthesis Of d proxyl nitroxide 16 with the proxyl group in the side chain of 1 is also described. A mild oxidation of 16 to the corresponding 3-keto spin label 17 in high yield is also achieved.

  DOI：

  10.1016/s0040-4020(01)92284-7
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 石胆酸 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 (R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid
  参考文献：
  名称：

  Novel biotinylated bile acid amphiphiles: Micellar aggregates formation and interaction with hepatocytes

  摘要：

  合成的两亲性胆汁酸通过寡聚乙二醇与生物素分子连接，在水环境中形成胶束结构，与阿维蛋白相互作用，并有效地与肝细胞结合，这表明它们具有作为肝病药物传输系统的潜力。

  DOI：

  10.1039/c0ob00878h

文献信息

• Lithocholic Acid Derivatives as Potent Vitamin D Receptor Agonists
  作者：Harue Sasaki、Hiroyuki Masuno、Haru Kawasaki、Ayana Yoshihara、Nobutaka Numoto、Nobutoshi Ito、Hiroaki Ishida、Keiko Yamamoto、Naoya Hirata、Yasunari Kanda、Emiko Kawachi、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1021/acs.jmedchem.0c01420

  日期：2021.1.14

  Lithocholic acid (2) was identified as a second endogenous ligand of vitamin D receptor (VDR), though its activity is very weak. In this study, we designed novel lithocholic acid derivatives based on the crystal structure of VDR–ligand-binding domain (LBD) bound to 2. Among the synthesized compounds, 6 bearing a 2-hydroxy-2-methylprop-1-yl group instead of the 3-hydroxy group at the 3α-position of

  Lithocholic acid (2) was identified as a second endogenous ligand of vitamin D receptor (VDR), though its activity is very weak. In this study, we designed novel lithocholic acid derivatives based on the crystal structure of VDR–ligand-binding domain (LBD) bound to 2. Among the synthesized compounds, 6 bearing a 2-hydroxy-2-methylprop-1-yl group instead of the 3-hydroxy group at the 3α-position of
• On The Protection of 3α-Hydroxy Group of A/B<i>cis</i>Steroids
  作者：Sharmila Banerjee Mukhopadhyay、Umesh R. Desai、Girish K. Trivedi

  DOI：10.1080/00397919108019755

  日期：1991.3

  The difficulties encountered in the protection of 3-alpha-hydroxy group of lithocholic acid 1 with three different types of protective groups are described. Only benzyl ether derivative was found to be suitable for synthetic transformations. The methodology for the synthesis of benzyl ethers of A/B cis steroids is reported for the first time.
• BANERJEE, SHARMILA;DESAI, UMESH R.;TRIVEDI, GIRISH K., SYNTH. COMMUN., 21,(1991) N, C. 757-770
  作者：BANERJEE, SHARMILA、DESAI, UMESH R.、TRIVEDI, GIRISH K.

  DOI：——

  日期：——