2-[(1S,2S,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxyethoxy)-2-(hydroxymethyl)cyclopentyl]ethyl acetate | 1220118-88-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-[(1S,2S,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxyethoxy)-2-(hydroxymethyl)cyclopentyl]ethyl acetate
• CAS: 1220118-88-6
• 化学式: C₂₀H₄₀O₆Si
• 分子量: 404.62
• InChiKey: MYIRZDZQXDJMGS-KXEXWTFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(1S,2S,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxyethoxy)-2-(hydroxymethyl)cyclopentyl]ethyl acetate 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到2-[(1S,2R,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxyethoxy)-2-formylcyclopentyl]ethyl acetate
  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：

  乙酸乙烯酯 、 2-[(1S,2S,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxyethoxy)-2-(hydroxymethyl)cyclopentyl]ethanol 在 Candida antarctica lipase B 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以88%的产率得到2-[(1S,2S,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxyethoxy)-2-(hydroxymethyl)cyclopentyl]ethyl acetate
  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