3β-acetoxylanost-8-en-25-ol | 42895-42-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-acetoxylanost-8-en-25-ol
• 英文别名: [(3S,5R,10S,13R,14R,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 42895-42-1
• 化学式: C₃₂H₅₄O₃
• 分子量: 486.779
• InChiKey: LIAVDDQFAHEVSE-RDXQEYJHSA-N

物化性质

• 熔点：
  167-169 °C(Solvent: Methanol)
• 沸点：
  539.6±50.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxylanost-8-en-25-ol 在 三溴化磷 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 25-aminosterols, new antifungal agents

  摘要：

  25-aminolanostenol 1 and 25-aminocholesterol 2 were hemisynthesized from natural sterols and tested in vitro against Candida albicans. The biological activity of compound 1 was rather weak, whereas 2 exhibited in vitro antifungal activity With MIC value of 4 mu M. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00233-4
• 作为产物：
  描述：

  (R)-methyl 4-((3S,5R,10S,13R,14R,17R)-3-acetoxy-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 在 乙醚 作用下， 生成 3β-acetoxylanost-8-en-25-ol
  参考文献：
  名称：

  Woodward et al., Journal of the Chemical Society, 1957, p. 1131,1141

  摘要：

  DOI：

文献信息

• Preparative Method for the Quantitative Separation of Methylenic Sterols from Unsaturated Sterol Mixtures by Chemoselective Hydroxymercuration-Deoxymercuration
  作者：Laïla El Kihel、Georges Charles

  DOI：10.1055/s-2006-942495

  日期：2006.8

  intermediates were easily purified by flash chromatography on silica gel column and the reactive alkenes were regenerated by deoxymercuration in a biphasic system (ethyl acetate/I M HCl, 2:1 ratio). These conditions leave the ring double bonds of steroids intact. No isomerization of methylene double bonds was observed.

  报道了一种前所未有的选择性和定量方法，允许从不饱和甾醇混合物中分离亚甲基甾醇。我们已将改良布朗条件下的羟基汞化反应扩展到对三十种不饱和甾醇作为各种甾醇混合物的系统研究。在甾醇的亚甲基侧链上实现了高产的定向化学选择性羟基汞化。得到的有机汞中间体很容易通过硅胶柱上的快速色谱法纯化，反应性烯烃通过在双相系统（乙酸乙酯/1M HCl，2:1比例）中脱氧汞再生。这些条件使类固醇的环双键完好无损。没有观察到亚甲基双键的异构化。
• RuCl3-TBHP mediated allylic oxidation of Δ8(9) lanosterol derivatives
  作者：Bapurao B. Shingate、Braja G. Hazra、Deepak B. Salunke、Vandana S. Pore

  DOI：10.1016/j.tetlet.2011.08.166

  日期：2011.11

  A variety of Δ8(9)-lanosterol derivatives were converted into 7,11-dienones using t-butyl hydroperoxide in the presence of ruthenium chloride (RuCl3) in good yields.

  在氯化钌（RuCl 3）存在下，使用叔丁基氢过氧化物将多种Δ8 （9）-羊毛甾醇衍生物转化为7,11-二烯酮。
• In vitro effects of oxygenated lanosterol derivatives on cholesterol biosynthesis from 24,25-dihydrolanosterol.
  作者：YOSHIKO SONODA、YOSHIO SEKIGAWA、YOSHIHIRO SATO

  DOI：10.1248/cpb.36.966

  日期：——

  The effects of oxygenated lanosterol derivatives (1-27, 5μM) including 32-oxygenated lanosterol derivatives on cholesterol biosyntheiss from [24, 25-3H2]-24, 25-dihydrolanosterol (18μM) were tested in 10000×g supernatant (S-10) fraction of rat liver homogenate. Among the derivatives, 7-oxolanost-8-en-3β-ol (7-oxo-DHL), 3β-acetoxylanost-8-en-7-one (7-oxo-DHL-3-OAc), and 7-oxolanosta-5, 8, 11-trien-3β-ol were highly active in depression cholesterol biosynthesis from 24, 25-dyhydrolanosterol. The inhibitory activities of these derivatives on cholesterol synthesis are discussed on the basis of the position and stereochemistry of the oxygen functional groups on the sterol nucleus. The effect of aphidicolin on cholesterol synthesis was also compared with that of 7-oxo-DHL.

  在10000×g上清液（S-10）中测试含氧羊毛甾醇衍生物（1-27, 5μM）（包括32-含氧羊毛甾醇衍生物）对[24, 25-3H2]-24, 25-二氢羊毛甾醇（18μM）胆固醇生物合成的影响) 大鼠肝匀浆的分数。其衍生物包括 7-oxolanost-8-en-3β-ol (7-oxo-DHL)、3β-acetoxylanost-8-en-7-one (7-oxo-DHL-3-OAc) 和 7-oxolanosta -5, 8, 11-trien-3β-ol 在 24, 25-二氢羊毛甾醇的抑郁胆固醇生物合成中具有高度活性。根据甾醇核上氧官能团的位置和立体化学讨论了这些衍生物对胆固醇合成的抑制活性。阿菲迪霉素对胆固醇合成的影响也与 7-oxo-DHL 进行了比较。
• Chemical synthesis
  申请人：Kavtaradze Kita Levan

  公开号：US20050038301A1

  公开（公告）日：2005-02-17

  The present invention relates to a method of producing vicinal diols from a compound, the method characterised by the step of reacting the compound with a moderately strong acid in the presence one or more reagents capable of supplying hydroxyl groups wherein the moderately strong acid is a strongly reducing agent, but has a conjugate base that is a weak nucleophile. In preferred embodiments the moderately strong acid is hypophosphorous acid and the reagent(s) capable of supplying hydroxyl groups is 2-propanol in water, where 2-propanol is water soluable and organic. This method is particularly applicable to the production of vicinal diols of steroids, including lanosterol. Once vicinal diols of lanosterol diols are formed they are then capable of being further reacted to produce high purity lanosterol.

  本发明涉及一种从化合物中制备邻二醇的方法，其特征在于将该化合物与中等强度酸在一种或多种能够提供羟基的试剂的存在下反应，其中中等强度酸是一种强还原剂，但具有弱亲核副基。在优选实施例中，中等强度酸是亚磷酸，能够提供羟基的试剂是水中的2-异丙醇，其中2-异丙醇是水溶性和有机的。该方法特别适用于类固醇，包括麦角甾醇的邻二醇的生产。一旦形成了麦角甾醇的邻二醇，它们就能够进一步反应，产生高纯度的麦角甾醇。
• Synthesis and antimicrobial activity of novel oxysterols from lanosterol
  作者：Bapurao B. Shingate、Braja G. Hazra、Deepak B. Salunke、Vandana S. Pore、Fazal Shirazi、Mukund V. Deshpande

  DOI：10.1016/j.tet.2013.10.090

  日期：2013.12

  Chemically diverse oxysterols and their synthetic manipulations were carried out from variety of Delta(8(9)_) lanosterol derivatives and evaluated for their in vitro antimicrobial activities. Most of the synthesized oxysterols exhibited significant antifungal activity against the tested strains. (C) 2013 Elsevier Ltd. All rights reserved.