(3R,4S,5S)-4-Benzyloxymethoxy-7-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol | 381247-14-9

• 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: (3R,4S,5S)-4-Benzyloxymethoxy-7-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol
• CAS: 381247-14-9
• 化学式: C₁₉H₃₂O₆
• 分子量: 356.459
• InChiKey: JPUUPTJEOUCGLJ-UVAUQZKFSA-N

物化性质

• 沸点：
  482.0±45.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  25.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-4-Benzyloxymethoxy-7-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol 在 palladium dihydroxide sodium periodate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 57.5h， 生成 (4R,5S,6S,E)-ethyl 5-hydroxy-8-(methoxymethoxy)-2,4,6-trimethyloct-2-enoate
  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 甲醇 、 锂硼氢 、 三甲基氯硅烷 、 草酰氯 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 (3R,4S,5S)-4-Benzyloxymethoxy-7-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol
  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