ethyl (1R,2R,3S,4R)-3-(tert-butyldimethylsiloxy)-2-((3aS,4S,5R,6aS)-4-isopropenyl-2,2-dimethyl-6-oxotetrahydrocyclopenta[1,3]dioxol-5-yl)-4-methyl-5-oxocyclopentane-1-carboxylate | 1003569-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1R,2R,3S,4R)-3-(tert-butyldimethylsiloxy)-2-((3aS,4S,5R,6aS)-4-isopropenyl-2,2-dimethyl-6-oxotetrahydrocyclopenta[1,3]dioxol-5-yl)-4-methyl-5-oxocyclopentane-1-carboxylate
• 英文别名: ethyl (1R,2R,3S,4R)-2-[(3aS,5R,6S,6aS)-2,2-dimethyl-4-oxo-6-prop-1-en-2-yl-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]-3-[tert-butyl(dimethyl)silyl]oxy-4-methyl-5-oxocyclopentane-1-carboxylate
• CAS: 1003569-97-8
• 化学式: C₂₆H₄₂O₇Si
• 分子量: 494.701
• InChiKey: SCLKRPNTQXSIOF-ZNUHCMCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl (3S,4R)-3-(tert-butyldimethylsiloxy)-4-methyl-5-oxocyclopent-1-enecarboxylate 、 ((3aS,6S,6aS)-6-isopropenyl-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yloxy)trimethylsilane 在 正丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 ethyl (1S,2S,3S,4R)-3-(tert-butyldimethylsiloxy)-2-((3aS,4S,5R,6aS)-4-isopropenyl-2,2-dimethyl-6-oxotetrahydrocyclopenta[1,3]dioxol-5-yl)-4-methyl-5-oxocyclopentane-1-carboxylate 、 ethyl (1R,2R,3S,4R)-3-(tert-butyldimethylsiloxy)-2-((3aS,4S,5R,6aS)-4-isopropenyl-2,2-dimethyl-6-oxotetrahydrocyclopenta[1,3]dioxol-5-yl)-4-methyl-5-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  Dramatic Solvent Effect on the Diastereoselectivity of Michael Addition:  Study toward the Synthesis of the ABC Ring System of Hexacyclinic Acid

  摘要：

  During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we have observed a dramatic influence of the solvent on both our key steps. The diastereoselectivity of the intermolecular Michael addition could be totally reversed by changing the polarity of the solvent, and trifluoroethanol was found to be the optimal solvent for the following Mn(III)-promoted radical cyclization.

  DOI：

  10.1021/ol702566c