(8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-iodo-21-norcholest-24-en-20-one | 442200-77-3

• 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: (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-iodo-21-norcholest-24-en-20-one
• 英文别名: 1-[(1S,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-(iodomethyl)-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-5-methylhex-4-en-1-one
• CAS: 442200-77-3
• 化学式: C₂₃H₄₁IO₂Si
• 分子量: 504.567
• InChiKey: FYYRHOGCJOFXNO-SQVLJLFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-iodo-21-norcholest-24-en-20-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 mercury(II) diacetate 、 四丁基氟化铵 、 silver(I) acetate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 206.75h， 生成 (8β)-(20R)-des-A,B-18,20-epoxy-25-[(methoxymethyl)oxy]-21-norcholestan-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 Jones's reagent 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 6.75h， 生成 (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-iodo-21-norcholest-24-en-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