benzyl (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoate | 1376112-94-5

• 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: benzyl (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoate
• 英文别名: Hexadecanoic acid, 2-hexyl-3-hydroxy-5-[(4-methoxyphenyl)methoxy]-, phenylmethyl ester, (2S,3S,5R)-；benzyl (2S,3S,5R)-2-hexyl-3-hydroxy-5-[(4-methoxyphenyl)methoxy]hexadecanoate
• CAS: 1376112-94-5
• 化学式: C₃₇H₅₈O₅
• 分子量: 582.865
• InChiKey: LVYIGOWBNUJIKK-SBPNQFBHSA-N

物化性质

• 沸点：
  669.4±55.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  42
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  benzyl (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoate 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 palladium on activated charcoal 、 2-甲基-6-硝基苯甲酸酐 、 水 、 氢气 、 碳酸氢钠 、 三乙胺 、 三苯基膦 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 19.0h， 生成 奥利司他
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r
• 作为产物：
  描述：

  (R)-3-(4-methoxybenzyloxy)tetradecanal 在 二异丙氧基二氯化钛 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.75h， 生成 benzyl (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoate
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r

文献信息

• J. Org. Chem. 2012, 77, 4885-4901
  作者：

  DOI：——

  日期：——