(4R,5S,6S,E)-2,4,6-trimethyl-5,8-bis((triethylsilyl)oxy)oct-2-en-1-yl pivalate | 381247-23-0

• 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: (4R,5S,6S,E)-2,4,6-trimethyl-5,8-bis((triethylsilyl)oxy)oct-2-en-1-yl pivalate
• CAS: 381247-23-0
• 化学式: C₂₈H₅₈O₄Si₂
• 分子量: 514.937
• InChiKey: VBQSOAOZSCYNDR-FLEMIFJZSA-N

物化性质

• 沸点：
  500.5±50.0 °C(Predicted)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  34.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S,E)-2,4,6-trimethyl-5,8-bis((triethylsilyl)oxy)oct-2-en-1-yl pivalate 在 水 manganese(IV) oxide 、 二氯二茂锆 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.67h， 生成 (4R,5S,6S)-9-iodo-2,4,6,8-tetramethyl-5-(triethylsilanyloxy)-nona-2,8-trans-dienal
  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：

  (3R,4S,5S)-4-Benzyloxymethoxy-7-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol 在 palladium dihydroxide 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 sodium periodate 、 B-溴代邻苯二氧硼烷 、 氢气 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 苯 为溶剂， 反应 99.5h， 生成 (4R,5S,6S,E)-2,4,6-trimethyl-5,8-bis((triethylsilyl)oxy)oct-2-en-1-yl pivalate
  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