(3E,5Z)-(2S)-5-tert-butyldimethylsilyloxy-1,2-isopropylidene-3,5-heptadiene | 850807-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3E,5Z)-(2S)-5-tert-butyldimethylsilyloxy-1,2-isopropylidene-3,5-heptadiene
• 英文别名: tert-butyl-[(1E,3Z)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]penta-1,3-dien-3-yl]oxy-dimethylsilane
• CAS: 850807-11-3
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: CBBCTFVDEFPKPT-GLBFHAHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3E,5Z)-(2S)-5-tert-butyldimethylsilyloxy-1,2-isopropylidene-3,5-heptadiene 在 三氟化硼乙醚 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 生成 (2S,3R,6S)-6-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methyl-2-((E)-2-phenylethenyl)tetrahydropyran-4-one
  参考文献：
  名称：

  Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes

  摘要：

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.

  DOI：

  10.1021/jo0488311
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (E)-(2S)-1,2-isopropylidene-3-hepten-5-one 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以92%的产率得到(3E,5Z)-(2S)-5-tert-butyldimethylsilyloxy-1,2-isopropylidene-3,5-heptadiene
  参考文献：
  名称：

  Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes

  摘要：

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.

  DOI：

  10.1021/jo0488311

文献信息

• Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes
  作者：Eelco Ruijter、Heike Schültingkemper、Ludger A. Wessjohann

  DOI：10.1021/jo0488311

  日期：2005.4.1

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.