methyl 3β-mesyloxycholate | 175340-06-4

• 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 3β-mesyloxycholate
• 英文别名: Methyl(3beta,5beta,7alpha,12alpha)-7,12-dihydroxy-3-(methanesulfonyloxy)cholan-24-oate；methyl (4R)-4-[(3S,5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-methylsulfonyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 175340-06-4
• 化学式: C₂₆H₄₄O₇S
• 分子量: 500.697
• InChiKey: BTVYUWGZLHLBJQ-SZNCYGQESA-N

物化性质

• 沸点：
  622.3±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3β-mesyloxycholate 在 sodium azide 、 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 4-{3-[4-(3-amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p
• 作为产物：
  描述：

  胆酸 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 乙酰氯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 methyl 3β-mesyloxycholate
  参考文献：
  名称：

  基于通过铜催化 [1,3]-偶极环加成获得的三芳基膦氧化物核的三足胆汁酸结构：合成和初步聚集研究

  摘要：

  我们报告了基于衍生自氧化三苯基膦的核心的新型水溶性、胆汁酸衍生的三足结构的合成和聚集行为。我们采用成熟的铜催化 [1,3]-偶极环加成 (CuAAC) 来构建这些三足分子。这些分子在水性介质中的聚集行为通过不同的分析方法进行研究，例如染料增溶、动态光散射、核磁共振和原子力显微镜。这些分子结构还提供了额外的优势，有助于理解胆汁酸骨架的性质和这些结构中类固醇 C-3 位置的构型的影响；据我们所知，这在文献中还没有报道。

  DOI：

  10.1002/ejoc.201301443

文献信息

• Mitsunobu reactions with methanesulfonic acid; The replacement of equatorial hydroxyl groups by azide with net retention of configuration
  作者：Anthony P. Davis、Stephan Dresen、Laurence J. Lawless

  DOI：10.1016/s0040-4039(97)00886-1

  日期：1997.6

  of equatorial cyclohexanols with Ph3P/DEAD/MsOH gives clean conversion to the axial mesylates. Subsequent reaction with NaN3 gives the equatorial azides in overall yields of 74–87%. Axial hydroxyl groups are not affected, allowing the regioselective conversion of methyl cholate into a 3α-azidodiol intermediate for steroid-based synthetic receptors.

  用Ph 3 P / DEAD / MsOH处理赤道环己醇可将其干净地转化为轴向甲磺酸酯。随后与NaN 3的反应使赤道叠氮化物的总产率为74-87％。轴向羟基不受影响，允许胆甾醇将区域选择性地转化为基于类固醇的合成受体的3α-叠氮二醇中间体。
• Improving reactivity and selectivity of aqueous-based Heck reactions by the local hydrophobicity of phosphine ligands
  作者：Gina M. Roberts、Shiyong Zhang、Yan Zhao、L. Keith Woo

  DOI：10.1016/j.tet.2015.09.010

  日期：2015.10

  affords a new ligand, 1, which is effective in palladium-catalyzed Heck cross-couplings between acrylates and aryl iodides under mild, aqueous reaction conditions. High yields, up to 99%, were achieved in water at 40 °C. In competition studies, a more hydrophobic substrate (n-Bu acrylate) was preferred over the least hydrophobic substrate (methyl acrylate), supportive of a localized hydrophobic microenvironment

  用胆酸盐部分的三芳基膦的变形，得到一个新的配体，1，这是有效的钯催化的Heck交叉偶联丙烯酸酯和芳基碘之间温和，含水反应条件下进行。在40°C的水中可实现高达99％的高收率。在竞争研究中，更疏水基质（Ñ -Bu丙烯酸酯）中的溶液，优选在至少疏水性基材（丙烯酸甲酯），支持靠近催化中心的局部微环境的疏水性的。当本地疏水性是使用标准的水溶性膦或在有机溶剂中消除了疏水性衬底的增强的反应性和选择性消失。
• Steroidal guanidines as enantioselective receptors for N-acyl α-amino acids. Part 1. 3α-Guanylated carbamates derived from cholic acid
  作者：Laurence J. Lawless、Adrian G. Blackburn、Alan J. Ayling、M. Nieves Pérez-Payán、Anthony P. Davis

  DOI：10.1039/b009215k

  日期：——

  other functional groups, were synthesized from cholic acid 1. These cations were shown to extract chiral carboxylate anions from aqueous buffer into chloroform with significant enantioselectivities. The most successful receptors bore two carbamate substituents and achieved, in the best cases, ratios (L:D) of 7–10:1 for a series of five N-acetyl α-amino acids.

  胆碱酸1合成了带有胍基，氨基甲酸酯和（在某些情况下）其他官能团的5-11受体。这些阳离子显示出从水缓冲液中将手性羧酸根阴离子提取到氯仿中的对映体选择性很高。最成功的受体带有两个氨基甲酸酯取代基，在最佳情况下，一系列五个N-乙酰基α-氨基酸的比率（L：D）达到7–10：1 。
• Novel glucocorticoid receptor ligands for the treatment of metabolic disorders
  申请人：——

  公开号：US20040235810A1

  公开（公告）日：2004-11-25

  This invention relates to novel compounds that are liver selective glucocorticoid receptor antagonists, to methods of preparing such compounds, and to methods for using such compounds in the regulation of metabolism, especially lowering serum glucose levels, insulin levels, or lipid levels, and/or decreasing body weight.

  本发明涉及一种肝脏选择性糖皮质激素受体拮抗剂的新化合物，涉及制备这种化合物的方法，以及利用这种化合物在调节新陈代谢方面的方法，特别是降低血清葡萄糖水平、胰岛素水平或脂质水平，和/或减轻体重。