(2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester | 183201-71-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester
• 英文别名: methyl (2S,3S,4R)-2-hydroxy-3,5-dimethyl-4-(phenylmethoxymethoxy)hexanoate
• CAS: 183201-71-0
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: ODHPPLRMIUIBNU-CWRNSKLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester 在 palladium dihydroxide 咪唑 、 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 pyridine-SO3 complex 、 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 38.5h， 生成 (1S)-1-[(4R,5S,6R)-6-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-prop-2-yn-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
• 作为产物：
  描述：

  D-缬氨酸 在 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 76.0h， 生成 (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl 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.