(8β)-(20R)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18,20-epoxy-21-norcholestan-25-ol | 442200-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (8β)-(20R)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18,20-epoxy-21-norcholestan-25-ol
• 英文别名: 5-[(3R,3aS,5aR,6S,9aS)-6-[tert-butyl(dimethyl)silyl]oxy-1,3,3a,4,5,5a,6,7,8,9-decahydroindeno[1,7a-c]furan-3-yl]-2-methylpentan-2-ol
• CAS: 442200-80-8
• 化学式: C₂₃H₄₄O₃Si
• 分子量: 396.686
• InChiKey: YFOKFWNFYPNPFU-SWMXPCKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (8β)-(20R)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18,20-epoxy-21-norcholestan-25-ol 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 正丁基锂 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (5Z,7E)-(1S,3R,20R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18,20-epoxy-25-[(methoxymethyl)oxy]-21-nor-9,10-secocholesta-5,7,10(19)-triene
  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-溴-3-甲基-2-丁烯 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 silver(I) acetate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 丙酮 为溶剂， 反应 178.5h， 生成 (8β)-(20R)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18,20-epoxy-21-norcholestan-25-ol
  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

文献信息

• Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization
  作者：Iván Cornella、José Pérez Sestelo、Antonio Mouriño、Luis A. Sarandeses

  DOI：10.1021/jo020022z

  日期：2002.7.1

  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.