methyl 3α-tosyloxycholan-24-oate | 1261-92-3

• 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-tosyloxycholan-24-oate
• 英文别名: methyl 3α-tosyloxy-5β-cholanoate；methyl 3α-tosyloxy-5β-cholan-24-oate；3α-tosyloxy-5β-cholan-24-oic acid methyl ester；methyl 3α-tosiloxy-5β-cholan-24-oate；(R)-methyl 4-((3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(tosyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate；3α-(toluene-4-sulfonyloxy)-5β-cholan-24-oic acid methyl ester；3α-(Toluol-4-sulfonyloxy)-5β-cholan-24-saeure-methylester；methyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(4-methylphenyl)sulfonyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1261-92-3
• 化学式: C₃₂H₄₈O₅S
• 分子量: 544.796
• InChiKey: SGOAEXLCEMXQRZ-SDHATHHKSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  614.2±28.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3α-tosyloxycholan-24-oate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以78%的产率得到5-Beta-卓兰-24-醇
  参考文献：
  名称：

  Cox; Nahar; Turner, Journal of Chemical Research - Part S, 2001, # 4, p. 162 - 164

  摘要：

  DOI：
• 作为产物：
  描述：

  石胆酸 在 吡啶 、 对甲苯磺酸 作用下， 反应 9.0h， 生成 methyl 3α-tosyloxycholan-24-oate
  参考文献：
  名称：

  Investigation on bile acid receptor regulators. Discovery of cholanoic acid derivatives with dual G-protein coupled bile acid receptor 1 (GPBAR1) antagonistic and farnesoid X receptor (FXR) modulatory activity

  摘要：

  Bile acids, the end products of cholesterol metabolism, activate multiple mechanisms through the interaction with membrane G-protein coupled receptors including the bile acid receptor GPBAR1 and nuclear receptors such as the bile acid sensor, farnesoid X receptor (FXR). Even if dual FXR/GPBAR1 agonists are largely considered a novel opportunity in the treatment of several liver and metabolic diseases, selective targeting of one of these receptors represents an attractive therapeutic approach for a wide range of disorders in which dual modulation is associated to severe side effects. In the present study we have investigated around the structure of LCA generating a small library of cholane derivatives, endowed with dual FXR agonism/GPBAR1 antagonism. To the best of our knowledge, this is the first report of bile acid derivatives able to antagonize GPBAR1. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.11.003

文献信息

• Potential bile acid metabolites. XV. Synthesis of 4.BETA.-hydroxylated bile acids; unique bile acids in human fetal bile.
  作者：Takashi IIDA、Toshiaki MOMOSE、Frederic C. CHANG、Junichi GOTO、Tosio NAMBARA

  DOI：10.1248/cpb.37.3323

  日期：——

  The 4 beta-hydroxylated derivatives of lithocholic, deoxycholic, chenodeoxycholic, and cholic acids were synthesized from their respective parent compounds. The principal reactions employed were 1) beta-face cis-dihydroxylation of delta 3 intermediates with osmium tetroxide-N-methylmorpholine N-oxide, 2) selective cathylation of vicinal 3 beta,4 beta-diols followed by oxidation of the resulting 4 beta-monocathylates

  由它们各自的母体化合物合成了石胆酸，脱氧胆酸，鹅去氧胆酸和胆酸的4个β-羟基化衍生物。所采用的主要反应是1）用四氧化-N-甲基吗啉N-氧化物对delta 3中间体进行β-面顺-二羟基化； 2）对邻位3 beta，4β-二醇进行选择性催化氧化，然后将所得4β-单羧酸盐，或用氯铬酸吡啶鎓在C-3处直接选择性氧化3个beta，4个β-二醇，以及3）用叔丁胺-硼烷络合物立体选择性还原3-氧代化合物。
• Selective, Transition Metal‐free 1,2‐Diboration of Alkyl Halides, Tosylates, and Alcohols
  作者：Mingming Huang、Jiefeng Hu、Shasha Shi、Alexandra Friedrich、Johannes Krebs、Stephen A. Westcott、Udo Radius、Todd B. Marder

  DOI：10.1002/chem.202200480

  日期：2022.4.27

  simple and efficient strategy to access alkyl 1,2-bis(boronate esters) via regio- and diastereoselective diboration of readily available secondary and tertiary alkyl halides (Br, Cl, I), tosylates, and alcohols was developed. The use of KI and DMA is critical to the methodology, which circumvents the regio- and diastereoselectivity problems. The transformation showed a broad substrate scope (75 examples)

  开发了一种无过渡金属、简单且有效的策略，通过对容易获得的仲和叔烷基卤化物（Br、Cl、I）、甲苯磺酸酯和醇进行区域和非对映选择性二硼化来获得烷基 1,2-双（硼酸酯） 。 KI 和 DMA 的使用对该方法至关重要，它可以避免区域选择性和非对映选择性问题。该转化显示了广泛的底物范围（75 个实例）以及天然产物后期修饰的实用性。
• Reductive Methylation of Steroid Ketones
  作者：John C. Babcock、Louis F. Fieser

  DOI：10.1021/ja01141a073

  日期：1952.11
• Seroflocculating Steroids. IV.¹ Unsaturated Bile Acid Esters²
  作者：Frederic C. Chang、Aaron Feldstein、Jane Ransom Gray、George S. McCaleb、Douglas H. Sprunt

  DOI：10.1021/ja01566a039

  日期：1957.5
• Nowak, P.; Blaszczyk , K.; Paryzek, Z., Organic Preparations and Procedures International, 1994, vol. 26, # 3, p. 374 - 376
  作者：Nowak, P.、Blaszczyk , K.、Paryzek, Z.

  DOI：——

  日期：——