(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-tert-butoxycarbonylamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester | 213338-56-8

• 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,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-tert-butoxycarbonylamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester
• 英文别名: methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-tris[(2-methylpropan-2-yl)oxycarbonylamino]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 213338-56-8
• 化学式: C₄₀H₆₉N₃O₈
• 分子量: 720.003
• InChiKey: JHRUNEYGHOBYAE-LJQRMKSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-tert-butoxycarbonylamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 在 cesium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid icosyl ester
  参考文献：
  名称：

  An Extraction-Based Assay for Neutral Anionophores: The Measurement of High Binding Constants to Steroidal Receptors in a Nonpolar Solvent

  摘要：

  The extraction-hased protocol for measuring binding constants. developed by Cram and co-workers, has been extended for use with anionic substrates. The method is especially useful for high-affinity receptors, allowing very high binding constants to tic measured in nonpolar solvents. Distribution constants K, between chloroform and water have been obtained for tetraethylammonium chloride and bromide, thus calibrating the method for these two substrates. Application to steroidal podands 5-9 has confirmed the ability of electron-withdrawing groups to enhance hydrogen-bond donor capabilities. Binding constants of approximate to 3 x 10(7) M-1 have been measured for the most powerful receptor 7 An X-ray crystal structure of 15. the methyl ester analogue of 7, reveals a well-defined binding site preorganised for anion recognition.

  DOI：

  10.1002/1521-3765(20020503)8:9<2197::aid-chem2197>3.0.co;2-j
• 作为产物：
  描述：

  胆酸 在 platinum(IV) oxide calcium hypochlorite 、 硫酸 、 盐酸羟胺 、 氢气 、 potassium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、5.88 MPa 条件下， 反应 125.0h， 生成 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-tert-butoxycarbonylamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester
  参考文献：
  名称：

  A Short Synthesis of Methyl 3α,7α,12α-Triaminocholanoate, the ‘Triaza-Analogue’ of Methyl Cholate

  摘要：

  三胺 2a 是一种面部双亲化合物，也是阴离子受体的前体，只需四个步骤就能从廉价的类固醇胆酸中制备出来。

  DOI：

  10.1055/s-2005-865221

文献信息

• The “triamino-analogue” of methyl cholate; a facial amphiphile and scaffold with potential for combinatorial and molecular recognition chemistry
  作者：Shay Broderick、Anthony P Davis、Robert P Williams

  DOI：10.1016/s0040-4039(98)01254-4

  日期：1998.8

  The triamino steroid 2 is synthesized from cholic acid (1), and found to possess little tendency to aggregate at pH 5 – 6 in aqueous solution. 2 and/or related derivatives are expected to find use in the synthesis of receptors and combinatorial libraries, and as “contrafacial amphiphiles” for drug delivery across cell membranes.

  三氨基甾族化合物2是由胆酸（1）合成的，在pH值为5 – 6的水溶液中几乎没有聚集的趋势。预期2和/或相关衍生物可用于受体和组合文库的合成中，并作为“反两亲物”用于跨细胞膜的药物递送。
• The "Triamino-analogue" of Methyl Cholate; A Practical, Large-Scale Synthesis
  作者：Anthony P. Davis、M. Nieves Pérez-Payán

  DOI：10.1055/s-1999-3114

  日期：——

  The triamino steroids 2 are in demand as facial amphiphiles and starting materials for supramolecular chemistry. 2 (R = Me) is now available from cholic acid 1 in substantial quantities via a new, high-yielding procedure.

  三氨基类固醇 2 作为面部双亲化合物和超分子化学的起始材料，需求量很大。现在，通过一种新的高产程序，可以从胆酸 1 中获得大量 2（R = Me）。
• An Extraction-Based Assay for Neutral Anionophores: The Measurement of High Binding Constants to Steroidal Receptors in a Nonpolar Solvent
  作者：Alan J. Ayling、Shay Broderick、John P. Clare、Anthony P. Davis、M. Nieves Pérez-Payán、Maarit Lahtinen、Maija J. Nissinen、Kari Rissanen

  DOI：10.1002/1521-3765(20020503)8:9<2197::aid-chem2197>3.0.co;2-j

  日期：2002.5.3

  The extraction-hased protocol for measuring binding constants. developed by Cram and co-workers, has been extended for use with anionic substrates. The method is especially useful for high-affinity receptors, allowing very high binding constants to tic measured in nonpolar solvents. Distribution constants K, between chloroform and water have been obtained for tetraethylammonium chloride and bromide, thus calibrating the method for these two substrates. Application to steroidal podands 5-9 has confirmed the ability of electron-withdrawing groups to enhance hydrogen-bond donor capabilities. Binding constants of approximate to 3 x 10(7) M-1 have been measured for the most powerful receptor 7 An X-ray crystal structure of 15. the methyl ester analogue of 7, reveals a well-defined binding site preorganised for anion recognition.
• A Short Synthesis of Methyl 3α,7α,12α-Triaminocholanoate, the ‘Triaza-Analogue’ of Methyl Cholate
  作者：Anthony Davis、Vicente del Amo、Khadga Bhattarai、Maija Nissinen、Kari Rissanen、M. Pérez-Payán

  DOI：10.1055/s-2005-865221

  日期：——

  Triamine 2a, a facial amphiphile and precursor for anion receptors, has been prepared in just four steps from the inexpensive steroid cholic acid.

  三胺 2a 是一种面部双亲化合物，也是阴离子受体的前体，只需四个步骤就能从廉价的类固醇胆酸中制备出来。