2β,3α-diacetoxy-5α-cholestane | 16126-33-3

• 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: 2β,3α-diacetoxy-5α-cholestane
• 英文别名: 2β,3α-Diacetoxy-5α-cholestan；(10S)-2c.3t-Diacetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；5α-Cholestandiyl-(2β.3α)-diacetat；[(2S,3S,5S,8R,9S,10S,13R,14S,17R)-2-acetyloxy-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: 16126-33-3
• 化学式: C₃₁H₅₂O₄
• 分子量: 488.751
• InChiKey: OXIWJSLKPDAMRJ-OBIXAAHCSA-N

物化性质

• 熔点：
  133-135 °C
• 沸点：
  529.4±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)：
  9.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2β,3α-diacetoxy-5α-cholestane 在 三乙胺三氧化硫 、 三丁基氧化锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 sodium 2β,3α-dihydroxy-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：

  2α,3α-epoxy-5α-cholestane 在 吡啶 、 溶剂黄146 作用下， 生成 2β,3α-diacetoxy-5α-cholestane
  参考文献：
  名称：

  关于类固醇和性激素。第160部分。2α，3α-和2β，3β-氧化胆甾烷；2-氧胆甾烷的构型

  摘要：

  确定了两个2，3-胆甾烯氧化物和两个2-氧胆甾烷的构型。在表胆固醇，胆固醇，2α-氧-胆固醇和2β-氧-胆甾烷的乙酸盐中，后者的乙酸盐最难皂化，这与模型考虑是一致的。

  DOI：

  10.1002/hlca.19490320139

文献信息

• Sterols. LXIII. 2,3-Dihydroxyandrostane Derivatives
  作者：Russell E. Marker、Louis. Plambeck

  DOI：10.1021/ja01875a006

  日期：1939.6

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