(5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene | 442200-75-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene
• 英文别名: 5-[(3R,3aS,7E,7aS)-7-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-3-prop-1-en-2-yl-2,3,4,5,6,7a-hexahydro-1H-inden-3a-yl]-2-methylpentan-2-ol
• CAS: 442200-75-1
• 化学式: C₃₉H₇₀O₃Si₂
• 分子量: 643.154
• InChiKey: VLCJJIHEOGHGLI-LYGCREONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.68
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以99%的产率得到(5Z,7E)-(1S,3R)-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene-1,3-diol
  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：

  (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-[2-(methoxycarbonyl)ethyl]-20-methyl-20-pregnene 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 28.0h， 生成 (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene
  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