3α-acetoxy-2β-hydroxy-5α-cholestane | 61010-51-3

• 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-acetoxy-2β-hydroxy-5α-cholestane
• 英文别名: 2β-hydroxycholestan-3α-yl acetate；[(2S,3S,5S,8R,9S,10S,13R,14S,17R)-2-hydroxy-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] acetate
• CAS: 61010-51-3
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: HFJDAIVNDINPBV-JOLYSRJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 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：

  3α-acetoxy-2β-hydroxy-5α-cholestane 在 吡啶 、 三乙胺三氧化硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 sodium 3α-acetoxy-2β-hydroxy-5α-cholestane-2-sulfate
  参考文献：
  名称：

  Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane

  摘要：

  Five new steroid sulfates, sodium 2beta,3alpha-dihydroxy-5alpha-cholestane 3-sulfate (6), sodium 2beta,3alpha-dihydroxy-5alpha-cholestane 2-sulfate (7), disodiurn 2beta,3alpha-dihydroxy-5alpha-cholestane disulfate (8), sodium 3alpha-acetoxy-2beta-hydroxy-5alpha-cholestane 2-sulfate (12), and sodium 2beta-acetoxy-3alpha-hydroxy-5alpha-cholestane 3-sulfate (13), have been synthesized starting from 3beta-hydroxy-5alpha-cholestane (1). The synthetic steroids were completely characterized by one-dimensional and two-dimensional NMR and FABMS spectra. Sulfation was performed using triethylaniine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The sulfated steroids were comparatively evaluated for their inhibitory effect on the replication of herpes simplex virus type 2 (HSV-2). Compounds 7 and 8 were the most effective in their inhibitory action against HSV-2. The disulfated steroid 8 also proved to be active against DEN-2 and JV. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00166-6
• 作为产物：
  描述：

  3β-(toluene-4-sulfonyloxy)-5α-cholestane 在 吡啶 、 硫酸 、 sodium carbonate 、 间氯过氧苯甲酸 、 三丁基氧化锡 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 58.5h， 生成 3α-acetoxy-2β-hydroxy-5α-cholestane
  参考文献：
  名称：

  Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane

  摘要：

  Five new steroid sulfates, sodium 2beta,3alpha-dihydroxy-5alpha-cholestane 3-sulfate (6), sodium 2beta,3alpha-dihydroxy-5alpha-cholestane 2-sulfate (7), disodiurn 2beta,3alpha-dihydroxy-5alpha-cholestane disulfate (8), sodium 3alpha-acetoxy-2beta-hydroxy-5alpha-cholestane 2-sulfate (12), and sodium 2beta-acetoxy-3alpha-hydroxy-5alpha-cholestane 3-sulfate (13), have been synthesized starting from 3beta-hydroxy-5alpha-cholestane (1). The synthetic steroids were completely characterized by one-dimensional and two-dimensional NMR and FABMS spectra. Sulfation was performed using triethylaniine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The sulfated steroids were comparatively evaluated for their inhibitory effect on the replication of herpes simplex virus type 2 (HSV-2). Compounds 7 and 8 were the most effective in their inhibitory action against HSV-2. The disulfated steroid 8 also proved to be active against DEN-2 and JV. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00166-6

文献信息

• Regioselective enzymatic acylation of vicinal diols of steroids
  作者：M. Manuel Cruz Silva、Sergio Riva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2005.01.104

  日期：2005.3

  Monoacylated derivatives of a complete set of 2,3- and 3,4-vicinal diols of steroids were prepared by regioselective lipase-catalysed transesterification reactions. The enzymes displayed different selectivities towards the vicinal diols depending on the configuration of the hydroxyl groups.

  完整的甾族化合物的2，3-和3，4-邻位二醇的单酰化衍生物是通过区域选择性脂肪酶催化的酯交换反应制备的。取决于羟基的构型，酶对邻二醇具有不同的选择性。