methyl 3α,7α,12α-triformyloxy-5β-cholanoate | 33744-75-1

• 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,7α,12α-triformyloxy-5β-cholanoate
• 英文别名: 3α,7α,12α-triformyloxy-5β-cholanoic acid-(24)-methyl ester；3α,7α,12α-Triformyloxy-5β-cholansaeure-(24)-methylester；methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-triformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 33744-75-1
• 化学式: C₂₈H₄₂O₈
• 分子量: 506.637
• InChiKey: KVLWXGDKSBUQJF-SREHDYERSA-N

物化性质

• 沸点：
  558.0±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3α,7α,12α-triformyloxy-5β-cholanoate 在 氢氧化钾 、 lithium hydroxide 、 苯亚硒酸酐 、 氨 、 氢气 、 lithium 、 potassium tri-sec-butyl-borohydride 、 亚碘酰苯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 8.33h， 生成 别胆酸
  参考文献：
  名称：

  Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids.

  摘要：

  描述了一种制备异胆酸和异胆酸的新的方法。合成的关键步骤是：1) 在苯基硒酸酐催化下，3α-羟基 5β-胆酸甲酯与碘氧苯的同时氧化-脱氢反应；2) 使用锂/液氨对1, 4-二烯-3-酮羟基酸的C-5进行还原异构化；3) 随后的3-酮 5α-化合物用K-Selectride进行还原。

  DOI：

  10.1248/cpb.41.763
• 作为产物：
  描述：

  胆酸 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 72.1h， 生成 methyl 3α,7α,12α-triformyloxy-5β-cholanoate
  参考文献：
  名称：

  Synthesis of cholic acid based calixpyrroles and porphyrins

  摘要：

  New cholic acid based calix[4]pyrroles and porphyrins were prepared and their properties were studied. It was confirmed by spectral measurements that the superassembly of 5, 15-bis(3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholan-24-yl)-10,20-diphenylporphyrin, the best candidate for this study from the conjugates prepared, may be influenced not only by the solvent mixture composition (polar/non-polar component ratio) but by time as well. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.04.008

文献信息

• A New Generation of “Cholaphanes”:  Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility
  作者：Khadga M. Bhattarai、Anthony P. Davis、Justin J. Perry、Christopher J. Walter、Stephan Menzer、David J. Williams

  DOI：10.1021/jo971272w

  日期：1997.11.1

  such as carbohydrates in nonpolar media. New features are the externally directed alkyl chains, promoting solubility in organic solvents, and (in the case of 3b/c) reduced conformational freedom resulting from truncation of the steroidal side-chain. In particular, modeling shows that the smallest macrocycle 3c possesses very little flexibility, preferring an open conformation which is also revealed in

  大环“胆甾烷” 3a-c由廉价的类固醇胆酸合成。像早期的亲戚一样，它们的特征是带有向内羟基的大量空腔，适用于在非极性介质中结合极性分子，例如碳水化合物。新功能是外部定向的烷基链，提高了在有机溶剂中的溶解度，并且（在3b / c的情况下）由于类固醇侧链的截断而降低了构象自由度。特别地，建模显示最小的大环3c具有非常小的柔性，优选开放构象，其也在其五水合物的X射线晶体结构中揭示。NMR研究表明，所有三个胆cho与CDCl（3）中的辛基β-D-葡萄糖苷形成1：1配合物，K（a）= 600-1560 M（-）（1）。胆甾烷3b / c被证明能够从水溶液中提取甲基β-D-葡萄糖苷到CHCl（3）中。对于3c，也证明了甲基β-D-葡萄糖苷通过氯仿屏障的转运。
• Über Steroide und Sexualhormone. (97. Mitteilung). Über Beziehungen zwischen Konstitution und optischer Drehung in der Cholsäure-Reihe
  作者：Pl. A. Plattner、H. Heusser

  DOI：10.1002/hlca.19440270193

  日期：——
• Hughes; Smith; Webb, Journal of the Chemical Society, 1949, p. 3437
  作者：Hughes、Smith、Webb

  DOI：——

  日期：——
• Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids.
  作者：Takashi IIDA、Shinji NISHIDA、Frederic C. CHANG、Toshifumi NIWA、Junichi GOTO、Toshio NAMBARA

  DOI：10.1248/cpb.41.763

  日期：——

  A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3α-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1, 4-dien-3-oxo hydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.

  描述了一种制备异胆酸和异胆酸的新的方法。合成的关键步骤是：1) 在苯基硒酸酐催化下，3α-羟基 5β-胆酸甲酯与碘氧苯的同时氧化-脱氢反应；2) 使用锂/液氨对1, 4-二烯-3-酮羟基酸的C-5进行还原异构化；3) 随后的3-酮 5α-化合物用K-Selectride进行还原。
• Synthesis of cholic acid based calixpyrroles and porphyrins
  作者：Thu Huong Nguyen Thi、Lenka Cardová、Michaela Dvořáková、Dagmar Ročková、Pavel Drašar

  DOI：10.1016/j.steroids.2012.04.008

  日期：2012.7

  New cholic acid based calix[4]pyrroles and porphyrins were prepared and their properties were studied. It was confirmed by spectral measurements that the superassembly of 5, 15-bis(3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholan-24-yl)-10,20-diphenylporphyrin, the best candidate for this study from the conjugates prepared, may be influenced not only by the solvent mixture composition (polar/non-polar component ratio) but by time as well. (c) 2012 Elsevier Inc. All rights reserved.