2,2-dimethylpropionic acid (4R,5S,6S)-8-oxo-2,4,6-trimethyl-5-(triethylsilanyloxy)-oct-2-trans-enyl ester | 381246-97-5

• 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: 2,2-dimethylpropionic acid (4R,5S,6S)-8-oxo-2,4,6-trimethyl-5-(triethylsilanyloxy)-oct-2-trans-enyl ester
• 英文别名: [(E,4R,5S,6S)-2,4,6-trimethyl-8-oxo-5-triethylsilyloxyoct-2-enyl] 2,2-dimethylpropanoate
• CAS: 381246-97-5
• 化学式: C₂₂H₄₂O₄Si
• 分子量: 398.659
• InChiKey: MDLFWORENJNYDQ-VARDCOAOSA-N

物化性质

• 沸点：
  440.3±45.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropionic acid (4R,5S,6S)-8-oxo-2,4,6-trimethyl-5-(triethylsilanyloxy)-oct-2-trans-enyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 4-二甲氨基吡啶 、 manganese(IV) oxide 、 氢氧化钾 、 二氯二茂锆 、 三苯胂 、 四丁基氟化铵 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 calcium carbonate 、 mercury dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 36.5h， 生成 巴佛洛霉素A1
  参考文献：
  名称：

  Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors

  摘要：

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.

  DOI：

  10.1021/ja011452u
• 作为产物：
  描述：

  2,2-dimethylpropionic acid (4R,5S,6S)-8-hydroxy-2,4,6-trimethyl-5-(triethylsilanyloxy)-oct-2-trans-enyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到2,2-dimethylpropionic acid (4R,5S,6S)-8-oxo-2,4,6-trimethyl-5-(triethylsilanyloxy)-oct-2-trans-enyl ester
  参考文献：
  名称：

  Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors

  摘要：

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.

  DOI：

  10.1021/ja011452u

文献信息

• Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors
  作者：Stephen Hanessian、Jianguo Ma、Wengui Wang

  DOI：10.1021/ja011452u

  日期：2001.10.1

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.