[2,2,3β,4,4-d5]-17,20:20,21-bismethylenedioxy-3α,11β-dihydroxy-5β-pregnan | 1338579-71-7

• 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: [2,2,3β,4,4-d5]-17,20:20,21-bismethylenedioxy-3α,11β-dihydroxy-5β-pregnan
• CAS: 1338579-71-7
• 化学式: C₂₃H₃₆O₆
• 分子量: 413.496
• InChiKey: AUOHAVCVBYCTCW-MBTZTEORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [2,2,3β,4,4-d5]-17,20:20,21-bismethylenedioxy-3α,11β-dihydroxy-5β-pregnan 在 吡啶 、 氢氟酸 、 sodium acetate 、 三甲基铵三氧化硫共聚物 、 pyridinium chlorochromate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 [2,2,3β,4,4-d5]-3α,17α-dihydroxy-21-sulfooxy-5β-pregnane-11,20-dione sodium
  参考文献：
  名称：

  Synthesis of 3- and 21-monosulfates of [2,2,3β,4,4-2H5]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry

  摘要：

  The 3- and 21-monosulfates of pentadeuterated 5 beta-tetrahydrocorticosteroides were synthesized, starting from cortisol and 11-deoxycotisol. The principal reactions used were (1) perdeuteration of the methylene groups adjacent to the 3-oxo group of 17,20:20,21-bismethylendioxy-5 beta-3-ketosteroids with NaOD in CH3OD followed by stereoselective reduction with NaBD4, (2) sulfation of hydroxy groups with sulfur trioxide-trimethylamine complex, and (3) removal of the 17,20:20,21-bismethylendioxy group with hydrogen fluoride. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.014
• 作为产物：
  描述：

  17,20:20,21-bismethylenedioxy-11β-hydroxy-5β-pregnan-3-one 在 sodium hydroxide 、 sodium borodeuteride 作用下， 以 1,4-二氧六环 、 CH₃OD 、 D₂D 、 重水 为溶剂， 反应 22.5h， 生成 [2,2,3β,4,4-d5]-17,20:20,21-bismethylenedioxy-3α,11β-dihydroxy-5β-pregnan
  参考文献：
  名称：

  Synthesis of 3- and 21-monosulfates of [2,2,3β,4,4-2H5]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry

  摘要：

  The 3- and 21-monosulfates of pentadeuterated 5 beta-tetrahydrocorticosteroides were synthesized, starting from cortisol and 11-deoxycotisol. The principal reactions used were (1) perdeuteration of the methylene groups adjacent to the 3-oxo group of 17,20:20,21-bismethylendioxy-5 beta-3-ketosteroids with NaOD in CH3OD followed by stereoselective reduction with NaBD4, (2) sulfation of hydroxy groups with sulfur trioxide-trimethylamine complex, and (3) removal of the 17,20:20,21-bismethylendioxy group with hydrogen fluoride. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.014