(3β,5α,8α,9β,10α,13α,14β,17α,20S)-3-(acetyloxy)cholan-24-oic acid methyl ester | 960525-66-0

• 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: (3β,5α,8α,9β,10α,13α,14β,17α,20S)-3-(acetyloxy)cholan-24-oic acid methyl ester
• 英文别名: methyl (4S)-4-[(3S,5S,8S,9R,10R,13S,14R,17S)-3-acetyloxy-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: 960525-66-0
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: DVIUCIPCTDVQAP-ACCPVXDNSA-N

物化性质

• 熔点：
  127-129 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  487.5±18.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β,5α,8α,9β,10α,13α,14β,17α,20S)-3-(acetyloxy)cholan-24-oic acid methyl ester 在 甲醇 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium acetate 、 silica gel 、 三乙胺 、 乙酰氯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (3β,5α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cholest-24-ene
  参考文献：
  名称：

  Synthesis of the enantiomer of the oxysterol-antagonist LY295427

  摘要：

  Cellular cholesterol homeostasis is regulated by oxygenated cholesterol metabolites called oxysterols. While the importance of oxysterols in the acute regulation of cholesterol homeostasis is known, the precise molecular mechanisms through which oxysterols exert their effects remain to be elucidated. LY295427 (1) is a known antagonist of the cholesterol-homeostatic effects of 25-hydroxycholesterol (25-HC), a biologically active oxysterol. In order to examine the mechanism of action of this antagonism, and to further explore recent evidence suggesting that the membrane effects of 25-HC contribute to acute cholesterol regulation, we synthesized the enantiomer of LY295427 (ent-LY295427). ent-LY295427 (2) will serve as a unique probe to provide insight into the role of transcription-independent mechanisms in regulation of cholesterol homeostasis. Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2011.03.008
• 作为产物：
  描述：

  (3β,5α,8α,9β,10α,13α,14β,20S,22E)-3-(acetyloxy)chola-16,22-dien-24-oic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(3β,5α,8α,9β,10α,13α,14β,17α,20S)-3-(acetyloxy)cholan-24-oic acid methyl ester
  参考文献：
  名称：

  Synthesis, Characterization, and Receptor Interaction Profiles of Enantiomeric Bile Acids

  摘要：

  Bile acids are endogenous steroid detergents with receptor-mediated physiologic actions including activation of the G-protein coupled receptor TGR5 and gene regulation mediated by nuclear receptors. In this study, we report the first synthesis of enantiomeric lithocholic acid (ent-LCA, ent-1) and chenodeoxycholic acid (ent-CDCA, ent-2) via ent-testosterone (3). ent-1 was synthesized in 21 total steps in 4.2% yield, whereas ent-2 was obtained in 23 total steps in 0.8% yield. Critical micelle concentrations of the enantiomeric bile acids were found to be identical to their natural counterparts. Furthermore, enantiomeric bile acids were also tested for their ability to modulate bile acid activated proteins: farnesoid X receptor, vitamin D receptor, pregnane X receptor, and TGR5. Interestingly, ent-1 and ent-2 showed differential interactions with these proteins as compared to their corresponding natural bile acids. These data highlight the potential for using enantioselectivity as away to distinguish between receptor and nonreceptor-mediated functions of natural bile acids.

  DOI：

  10.1021/jm0707931

表征谱图