(2S,6aS,6bR,7S,8aS,8bS,10S,11aR,12aS,12bS)-2,6b-difluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-10-(4-((3-(methylthio)phenyl)thio)phenyl)-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4-one | 1365915-07-6

• 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: (2S,6aS,6bR,7S,8aS,8bS,10S,11aR,12aS,12bS)-2,6b-difluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-10-(4-((3-(methylthio)phenyl)thio)phenyl)-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4-one
• CAS: 1365915-07-6
• 化学式: C₃₅H₃₆F₂O₆S₂
• 分子量: 654.796
• InChiKey: HOYVAXGUMWVTKK-HWIYRGLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  醋酸氟轻松 在 tetrafluoroboric acid 、 三氟甲磺酸 、 magnesium sulfate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 (4aS,4bR,5S,6aS,6bS,8R,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a-dimethyl-8-(4-{[3-(methylthio)phenyl]thio}phenyl)-4a,4b,5,6,6a,6-b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho-[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one 、 (2S,6aS,6bR,7S,8aS,8bS,10S,11aR,12aS,12bS)-2,6b-difluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-10-(4-((3-(methylthio)phenyl)thio)phenyl)-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4-one
  参考文献：
  名称：

  Kilogram-Scale Synthesis of an Inhaled Corticosteroid

  摘要：

  The development and implementation of a safe and scalable process for the manufacture of corticosteroid PF-4714224 (1) is described. Initial routes used to synthesise analogues from this series directly from fluocinolone acetonide (2) were unsuitable for large-scale use. Key aspects of the route are the efficient and simple method for the preparation of the steroid tetraol (6), acetal formation by reaction of the tetraol with a bisulphite adduct (12), and isolation of the product by sequential recrystallisations.

  DOI：

  10.1021/op200257g