3α-cholestanyl mesylate | 3381-53-1

• 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: 3α-cholestanyl mesylate
• 英文别名: [(3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] methanesulfonate
• CAS: 3381-53-1
• 化学式: C₂₈H₅₀O₃S
• 分子量: 466.769
• InChiKey: KTDRRIFHPBRCMS-UIALXTEESA-N

物化性质

• 沸点：
  551.9±17.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-cholestanyl mesylate 在 ion-exchange resin - form> 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 3β-fluoro-5α-cholestane
  参考文献：
  名称：

  Colonna,S. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 2248 - 2252

  摘要：

  DOI：
• 作为产物：
  描述：

  5-alpha-胆甾烷-3-alpha-醇乙酸酯 在 吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3α-cholestanyl mesylate
  参考文献：
  名称：

  氯甲烷磺酸盐与乙酸铯反应转化仲醇的有效方法

  摘要：

  已经进行了使用（氯甲基磺酰基）氧基作为有利的离去基团在18-冠-6存在下用乙酸铯转化各种仲醇的方法，从而以高收率得到了转化的乙酸酯。

  DOI：

  10.1016/0040-4039(96)01333-0

文献信息

• Mitsunobu reactions with methanesulfonic acid; The replacement of equatorial hydroxyl groups by azide with net retention of configuration
  作者：Anthony P. Davis、Stephan Dresen、Laurence J. Lawless

  DOI：10.1016/s0040-4039(97)00886-1

  日期：1997.6

  of equatorial cyclohexanols with Ph3P/DEAD/MsOH gives clean conversion to the axial mesylates. Subsequent reaction with NaN3 gives the equatorial azides in overall yields of 74–87%. Axial hydroxyl groups are not affected, allowing the regioselective conversion of methyl cholate into a 3α-azidodiol intermediate for steroid-based synthetic receptors.

  用Ph 3 P / DEAD / MsOH处理赤道环己醇可将其干净地转化为轴向甲磺酸酯。随后与NaN 3的反应使赤道叠氮化物的总产率为74-87％。轴向羟基不受影响，允许胆甾醇将区域选择性地转化为基于类固醇的合成受体的3α-叠氮二醇中间体。
• Group 4 metallocene complexes bearing cholestanol-derived substituents at the Cp-rings— their synthesis and use in propene polymerization catalysis
  作者：Gerhard Erker、Christoph Mollenkopf

  DOI：10.1016/0022-328x(94)87161-2

  日期：1994.12

  corresponding fulvene, methyl lithium was added and deprotonation and addition to ZrCl4(THF)2 furnished bis[η5-(3β-methyl- 5α-cholestan-3α-yl)cyclopentadienyl]zirconium dichloride (11b). Treatment of the chiral Cp-substituted zirconocene dichlorides with a large excess of methyl alumoxane gave homogeneous Ziegler catalysts. Propene polymerization proceeded with overall stereochemical chain end control to

  制备了在Cp环上带有胆固醇衍生的取代基的两个系列的第4族弯曲金属茂配合物。5α-Cholestan-3α-ol被转化为3α-甲磺酸酯。亲核取代CpNa，随后去质子化和治疗的ZrCl 4（THF）2，得到双[η 5 - （5α-胆甾烷3β基）环戊二烯基]二氯化锆3β- 5。5α-胆甾烷-3-酮6被转化成相应的富烯中，加入甲基锂和去质子化和除的ZrCl 4（THF）2个布置双[η 5 - （3β甲基5α-胆甾烷3α基）环戊二烯基]二氯化锆（11b）。用大量过量的甲基铝氧烷处理手性Cp-取代的锆茂二氯化物得到均相的齐格勒催化剂。丙烯聚合进行整体立体化学链端控制，得到部分全同立构的聚丙烯。
• 77Se,13C and1H NMR spectra of phenylselenenylcycloalkanes, -cycloalkenes and some of their selenoxides and125Te NMR of a tellurium analogue
  作者：Helmut Duddeck、Petra Wagner、Armin Biallaß

  DOI：10.1002/mrc.1260290310

  日期：1991.3

  The 77Se, 13C and 1H NMR spectra of 46 mostly new compounds with phenylselenenyl groups attached to carbocycles and of three new corresponding selenoxides and the 125Te NMR of phenyltellurenylcyclohexane are reported. Substituent effects on the chemical shifts of these nuclei are compiled and discussed in terms of the configuration and conformation. Low-temperature NMR spectra of some cyclohexane derivatives allowed the evaluation of thermodynamic data, such as A values of the PhSe, PhSe(O) and PhTe groups.

  报道了46个主要为新化合物（具有连接到碳环上的苯基亚硒基团）以及三个新的相应亚硒氧化物的77Se、13C和1H NMR光谱，以及苯基碲基环己烷的125Te NMR光谱。根据构型和构象，对这些核的化学位移的取代基效应进行了汇编和讨论。一些环己烷衍生物的低温NMR光谱使得能够评估热力学数据，例如PhSe、PhSe(O)和PhTe基团的A值。
• Evaluation of steroidal amines as lipid raft modulators and potential anti-influenza agents
  作者：Sameer Agarwal、Cornelia Schroeder、Georg Schlechtingen、Tobias Braxmeier、Gary Jennings、Hans-Joachim Knölker

  DOI：10.1016/j.bmcl.2013.07.015

  日期：2013.9

  The influenza A virus (IFV) possesses a highly ordered cholesterol-rich lipid envelope. A specific composition and structure of this membrane raft envelope are essential for viral entry into cells and virus budding. Several steroidal amines were investigated for antiviral activity against IFV. Both, a positively charged amino function and the highly hydrophobic (ClogP >= 5.9) ring system are required for IC50 values in the low mu M range. An amino substituent is preferential to an azacyclic A-ring. We showed that these compounds either disrupt or augment membrane rafts and in some cases inactivate the free virus. Some of the compounds also interfere with virus budding. The antiviral selectivity improved in the series 3-amino, 3-aminomethyl, 3-aminoethyl, or by introducing an OH function in the A-ring. Steroidal amines show a new mode of antiviral action in directly targeting the virus envelope and its biological functions. (C) 2013 Elsevier Ltd. All rights reserved.
• Ahmed,S. et al., Australian Journal of Chemistry, 1971, vol. 24, p. 521 - 547
  作者：Ahmed,S. et al.

  DOI：——

  日期：——