2,2-dimethylpropionic acid (2S,3R,4R)-4-benzyloxymethoxy-2-(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl ester | 381246-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dimethylpropionic acid (2S,3R,4R)-4-benzyloxymethoxy-2-(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl ester
• 英文别名: [(2S,3R,4R)-2-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-4-(phenylmethoxymethoxy)hexyl] 2,2-dimethylpropanoate
• CAS: 381246-77-1
• 化学式: C₂₇H₄₈O₅Si
• 分子量: 480.761
• InChiKey: HWEMKFCQNMSEST-QPTUXGOLSA-N

物化性质

• 沸点：
  495.9±45.0 °C(predicted)
• 密度：
  0.969±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropionic acid (2S,3R,4R)-4-benzyloxymethoxy-2-(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl ester 在 palladium dihydroxide 咪唑 、 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 pyridine-SO3 complex 、 potassium tert-butylate 、 四丁基氟化铵 、 氢气 、 碘 、 叔丁基锂 、 二异丁基氢化铝 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxane
  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：

  D-缬氨酸 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 草酰氯 、 硫酸 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 90.0h， 生成 2,2-dimethylpropionic acid (2S,3R,4R)-4-benzyloxymethoxy-2-(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl 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.