3β-tetrahydropyranyloxycholest-5-en-24-one | 58497-30-6

• 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-tetrahydropyranyloxycholest-5-en-24-one
• 英文别名: 3β-((Ξ)-tetrahydropyran-2-yloxy)-cholest-5-en-24-one；3β-((Ξ)-Tetrahydropyran-2-yloxy)-cholest-5-en-24-on；3β-[(tetrahydro-2H-pyran-2-yl)oxy]cholest-5-en-24-on；(6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-one
• CAS: 58497-30-6
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: VWACKMMVKOUYRB-MSJAMATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-tetrahydropyranyloxycholest-5-en-24-one 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以1.8 g的产率得到24-oxocholesterol
  参考文献：
  名称：

  摘要：

  The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.

  DOI：

  10.1023/a:1015720707433
• 作为产物：
  描述：

  3B-羟基-D5-胆烯酸 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 锂硼氢 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 44.67h， 生成 3β-tetrahydropyranyloxycholest-5-en-24-one
  参考文献：
  名称：

  摘要：

  The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.

  DOI：

  10.1023/a:1015720707433

文献信息

• Biosynthesis of 24β-alkyl-Δ25-sterols in hairy roots of Ajuga reptans var. atropurpurea
  作者：Tomoko Yagi、Masuo Morisaki、Tetsuo Kushiro、Hiroko Yoshida、Yoshinori Fujimoto

  DOI：10.1016/0031-9422(95)00766-0

  日期：1996.3

  A hairy root culture of Ajuga reptans var. atropurpurea contains clerosterol, 22-dehydroclerosterol and cholesterol as its sterol constituents. Feeding of [26-, 27-13C2]desmosterol to this culture and 13C NMR analysis of the resulting biosynthesized sterols showed that the substrate was efficiently incorporated into clerosterol and codisterol. Feeding of [26-13C] and [27-13C]desmosterols revealed that

  Ajuga reptans var. 的毛状根培养物。atropurpurea 含有作为其甾醇成分的硬甾醇、22-脱氢硬甾醇和胆固醇。将 [26-, 27-13C2] 去甾醇加入到该培养物中，并对所得生物合成甾醇进行 13C NMR 分析，结果表明底物有效地掺入了硬甾醇和辅甾醇中。[26-13C] 和 [27-13C]desmosterols 的进料表明 C-24 烷基化以高度特异性的方式发生，其中底物的 26-和 27-甲基变成 C-26（乙烯基甲基）和 C -27（外亚甲基碳），分别为两种 Δ25-甾醇。此外，[24-2H]desmosterol的进料和产物的2H NMR分析表明，clerosterol和codisterol的H-24衍生自desmosterol的H-24。最后，[28-13C]ergosta-5，24(28)-dien-3β-ol 被证明可以转化为 clesterol
• Meiosis regulating compounds
  申请人：——

  公开号：US20010005757A1

  公开（公告）日：2001-06-28

  Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula 1 wherein the substituents are as defined in the specification.

  某些化合物在结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，可用于调节卵母细胞和男性生殖细胞中的减数分裂。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。这些化合物具有结构式，其中取代基如规范中定义。
• New 25-hydroxy-24-oxocholestane derivatives and preparation thereof
  申请人：TEIJIN LIMITED

  公开号：EP0015122A1

  公开（公告）日：1980-09-03

  The novel 25-hydroxy-24-oxocholestane derivatives of this invention can easily be converted to 24,25-dihydroxycholecalciferol or 1α,24,25-trihydroxycholecalciferol which is known as useful for medicine controlling the calcium metabolism of warm-blooded animals. Moreover, 25-hydroxy-24-oxocholestane derivatives can be converted to novel 25-hydroxy-24- oxocholecalciferol expressed by the following formula and novel 1 α,25-dihydroxy-24-oxocholecalciferol of the formula

  本发明的新型 25-hydroxy-24-oxocholestane 衍生物可以很容易地转化为 24,25-二羟基胆钙化醇或 1α,24,25-三羟基胆钙化醇，后者是众所周知的用于控制温血动物钙代谢的药物。此外，25-羟基-24-氧代胆甾烷衍生物可转化为新型 25-羟基-24-氧代胆钙化醇，如下式所示 和新型 1 α,25-二羟基-24-氧代胆钙化醇，其式为
• Contributions to the Study of Marine Products. XLIX. Synthesis of 29-Isofucosterol^1,2
  作者：JOHN P. DUSZA

  DOI：10.1021/jo01071a026

  日期：1960.1
• Bergmann; Dusza, Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 36,41
  作者：Bergmann、Dusza

  DOI：——

  日期：——