(8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-[2-(methoxycarbonyl)ethyl]pregnan-20-one | 442200-68-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-[2-(methoxycarbonyl)ethyl]pregnan-20-one
• 英文别名: methyl 4-[(3S,3aR,7S,7aR)-3-acetyl-7-[tert-butyl(dimethyl)silyl]oxy-1,2,3,4,5,6,7,7a-octahydroinden-3a-yl]butanoate
• CAS: 442200-68-2
• 化学式: C₂₂H₄₀O₄Si
• 分子量: 396.643
• InChiKey: CDAHEOVIWICBRD-GHDARCQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-[2-(methoxycarbonyl)ethyl]pregnan-20-one 在 重铬酸吡啶 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 48.25h， 生成 des-A,B-18-[2-(methoxycarbonyl)ethyl]-20-methylpregn-20-en-8-one
  参考文献：
  名称：

  Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization

  摘要：

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.

  DOI：

  10.1021/jo020022z
• 作为产物：
  描述：

  1-[(1S,3aR,4S,7aS)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-iodomethyl-octahydro-inden-1-yl]-ethanol 在 copper(l) iodide 、 Jones's reagent 、 锌 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-[2-(methoxycarbonyl)ethyl]pregnan-20-one
  参考文献：
  名称：

  Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization

  摘要：

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.

  DOI：

  10.1021/jo020022z