(4R,5S,6S,E)-8-(methoxymethoxy)-2,4,6-trimethyl-5-((triethylsilyl)oxy)oct-2-en-1-ol | 381247-16-1

• 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)-8-(methoxymethoxy)-2,4,6-trimethyl-5-((triethylsilyl)oxy)oct-2-en-1-ol
• CAS: 381247-16-1
• 化学式: C₁₉H₄₀O₄Si
• 分子量: 360.61
• InChiKey: DYOKTWKOMCQIAF-LCUJEDGHSA-N

物化性质

• 沸点：
  407.4±45.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S,E)-8-(methoxymethoxy)-2,4,6-trimethyl-5-((triethylsilyl)oxy)oct-2-en-1-ol 在 吡啶 、 B-溴代邻苯二氧硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 2,2-dimethylpropionic acid (4R,5S,6S)-5,8-dihydroxy-2,4,6-trimethyl-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
• 作为产物：
  描述：

  (7S,8S)-8-((benzyloxy)methoxy)-7,12,12-trimethyl-11,11-diphenyl-2,4,10-trioxa-11-silatridecane 在 palladium dihydroxide 咪唑 、 甲醇 、 sodium periodate 、 锂硼氢 、 三甲基氯硅烷 、 草酰氯 、 四丁基氟化铵 、 氢气 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 苯 为溶剂， 反应 107.5h， 生成 (4R,5S,6S,E)-8-(methoxymethoxy)-2,4,6-trimethyl-5-((triethylsilyl)oxy)oct-2-en-1-ol
  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