[2,2,3β,4,4-d5]-3α,17α-dihydroxy-21-sulfooxy-5β-pregnane-11,20-dione sodium | 1338579-83-1

• 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: [2,2,3β,4,4-d5]-3α,17α-dihydroxy-21-sulfooxy-5β-pregnane-11,20-dione sodium
• 英文别名: [2,2,3β,4,4-d5]-THE-21 sulfate sodium；sodium;[2-oxo-2-[(3R,5R,8S,9S,10S,13S,14S,17R)-2,2,3,4,4-pentadeuterio-3,17-dihydroxy-10,13-dimethyl-11-oxo-1,5,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] sulfate
• CAS: 1338579-83-1
• 化学式: C₂₁H₃₁O₈S*Na
• 分子量: 471.488
• InChiKey: HRAJSGIZFYLPNC-DNOFALGHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.65
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以13 mg的产率得到[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