15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-5β-pregnan-3-one | 187406-87-7

• 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: 15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-5β-pregnan-3-one
• CAS: 187406-87-7
• 化学式: C₂₅H₃₈O₆
• 分子量: 434.573
• InChiKey: SGWXLGWEQWAWSI-PMLBTZDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-5β-pregnan-3-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 15β-acetoxy-20,20-ethylenedioxy-5β-pregnan-3α,17α-diol
  参考文献：
  名称：

  15β-hydroxysteroids (part VII). Steroids of the human perinatal period: The synthesis of steroid markers and their radioactive tracers

  摘要：

  We report the synthesis of 10 novel steroids obtained from 3 beta,15 beta-diacetoxy-17 alpha-hydroxy-5-pregnen-20-one (1c) as intermediates in the synthesis of 15 beta-acetoxy-2,20-ethylenedioxy-17 alpha-hydroxy-4-pregnen-3-one (6a) and its tritiated tracer 15 beta-acetoxy-20,20-ethylenedioxy-17 alpha-hydroxy-1,2,6,7-H-3-pregn-4-en-3-one (6d). The one pot interconversion of intermediate (6a) to 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1a) and 3 alpha,15 beta,17 alpha-trihydroxy-5 beta-pregnan-20-one (2a) provides a new and efficient approach to the synthesis of diagnostically important metabolites of the human neonate and a possible route in the synthesis of the tritated tracers 3 beta,15 beta,17 alpha-trihydroxy-1,2,7-H-3-pregn-5-en-20-one (1d) and 3 alpha,15 beta,17 alpha-trihydroxy-1,2,6,7-H-3-5 beta-pregnan-20-one (2b) for the development of new immunoassays. We also report in this investigation an alternative route in the synthesis of 15 beta,17 alpha-dihydroxy-4-pregnen-3,20-dione (7a) an intermediate in the synthesis of human 15 beta-hydroxysteroid metabolites. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00204-8
• 作为产物：
  描述：

  Acetic acid (8R,9S,10R,13S,14S,15R,17R)-17-hydroxy-10,13-dimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-3-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl ester 在 Rh on carbon 吡啶 、 sodium tetrahydroborate 、 氢气 、 二乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 14.17h， 生成 15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-5β-pregnan-3-one
  参考文献：
  名称：

  15β-hydroxysteroids (part VII). Steroids of the human perinatal period: The synthesis of steroid markers and their radioactive tracers

  摘要：

  We report the synthesis of 10 novel steroids obtained from 3 beta,15 beta-diacetoxy-17 alpha-hydroxy-5-pregnen-20-one (1c) as intermediates in the synthesis of 15 beta-acetoxy-2,20-ethylenedioxy-17 alpha-hydroxy-4-pregnen-3-one (6a) and its tritiated tracer 15 beta-acetoxy-20,20-ethylenedioxy-17 alpha-hydroxy-1,2,6,7-H-3-pregn-4-en-3-one (6d). The one pot interconversion of intermediate (6a) to 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1a) and 3 alpha,15 beta,17 alpha-trihydroxy-5 beta-pregnan-20-one (2a) provides a new and efficient approach to the synthesis of diagnostically important metabolites of the human neonate and a possible route in the synthesis of the tritated tracers 3 beta,15 beta,17 alpha-trihydroxy-1,2,7-H-3-pregn-5-en-20-one (1d) and 3 alpha,15 beta,17 alpha-trihydroxy-1,2,6,7-H-3-5 beta-pregnan-20-one (2b) for the development of new immunoassays. We also report in this investigation an alternative route in the synthesis of 15 beta,17 alpha-dihydroxy-4-pregnen-3,20-dione (7a) an intermediate in the synthesis of human 15 beta-hydroxysteroid metabolites. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00204-8