methyl (Z)-7-[(1S,2R,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-hydroxycyclopentyl]hept-5-enoate | 1220118-97-7

• 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: methyl (Z)-7-[(1S,2R,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-hydroxycyclopentyl]hept-5-enoate
• CAS: 1220118-97-7
• 化学式: C₃₃H₆₄O₅Si₂
• 分子量: 597.039
• InChiKey: BVEBTQSKRXGTHF-XEDMQEKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (Z)-7-[(1S,2R,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-hydroxycyclopentyl]hept-5-enoate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Total Synthesis of 15-D_2t- and 15-epi-15-E_2t-Isoprostanes

  摘要：

  The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.

  DOI：

  10.1021/jo1000274
• 作为产物：
  描述：

  methyl (Z)-7-[(1S,2R,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-(1-ethoxyethoxy)cyclopentyl]hept-5-enoate 在 乙醇 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以75%的产率得到methyl (Z)-7-[(1S,2R,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-hydroxycyclopentyl]hept-5-enoate
  参考文献：
  名称：

  Total Synthesis of 15-D_2t- and 15-epi-15-E_2t-Isoprostanes

  摘要：

  The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.

  DOI：

  10.1021/jo1000274