5,6β-epoxy-5β-sitostan-3β-ol acetate | 125225-08-3

• 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: 5,6β-epoxy-5β-sitostan-3β-ol acetate
• 英文别名: 3β-acetoxy-5,6β-epoxystigmastane；[(1S,2R,5S,7S,9R,11S,12S,15R,16R)-15-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-yl] acetate
• CAS: 125225-08-3
• 化学式: C₃₁H₅₂O₃
• 分子量: 472.752
• InChiKey: UZDSGVFJNPWYPD-UEVLGMLBSA-N

物化性质

• 沸点：
  527.1±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6β-epoxy-5β-sitostan-3β-ol acetate 在 NaCO₃ 作用下， 以 甲醇 、 水 为溶剂， 以87%的产率得到(24R)-5β,6β-epoxy-24-ethylcholestane-3β-ol
  参考文献：
  名称：

  Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides

  摘要：

  An effective purification method for P-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. P-Sitosterol (>= 95% purity) was obtained on a gram-scale. Thus, the synthesis of six P-sitosterol oxides, including 7 alpha-hydroxy, 7 beta-hydroxy, 5,6 alpha-epoxy, 5,6 beta-epoxy, 7-keto, and 5 alpha,6 beta-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (similar to 95% purity) were well-documented. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.06.003
• 作为产物：
  描述：

  3β-acetoxy-5α-bromo-6β-hydroxystigmastane 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到5,6β-epoxy-5β-sitostan-3β-ol acetate
  参考文献：
  名称：

  Synthesis of highly pure oxyphytosterols and (oxy)phytosterol estersPart I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols

  摘要：

  The synthesis of several oxyphytosterols is described starting from stigmasterol, the key step being the regioselective hydrogenation of the 22-23 double bond of the latter. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.02.004

文献信息

• Convenient synthesis of chlorohydrins from epoxides using zinc oxide: Application to 5,6-epoxysitosterol
  作者：Firouz Matloubi Moghaddam、Hamdollah Saeidian、Zohreh Mirjafary、Marjan Jebeli Javan、Mehdi Moridi Farimani、Marjan Seirafi

  DOI：10.1002/hc.20529

  日期：——

  Efficient synthesis of protected and unprotected chlorohydrins has been achieved by ring opening of epoxides with acetyl/benzoyl chloride and TMSCl using a catalytic amount of ZnO as a reusable catalyst. The applicability of ZnO is further extended by performing the cleavage of the natural product 5,6-epoxysitosterol with acetyl chloride. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:157–163, 2009;

  使用催化量的 ZnO 作为可重复使用的催化剂，通过环氧化物与乙酰基/苯甲酰氯和 TMSCl 的开环，实现了受保护和未受保护的氯醇的有效合成。通过用乙酰氯对天然产物 5,6-环氧谷甾醇进行裂解，进一步扩展了 ZnO 的适用性。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:157–163, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20529
• A concise synthesis of β-sitosterol and other phytosterols
  作者：Jiliang Hang、Patrick Dussault

  DOI：10.1016/j.steroids.2010.05.016

  日期：2010.12

  A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of beta-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Delta(22-23) phytosterols. (C) 2010 Elsevier Inc. All rights reserved.
• GALAGOVSKY, L.;BURTON, G.;GROS, E. G., Z. NATURFORSCH. B , 44,(1989) N, C. 806-810
  作者：GALAGOVSKY, L.、BURTON, G.、GROS, E. G.

  DOI：——

  日期：——