(2S,3S,5R)-2-hexyl-3-hydroxy-5-(triisopropylsilyloxy)hexadecanoic acid | 296242-38-1

• 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,5R)-2-hexyl-3-hydroxy-5-(triisopropylsilyloxy)hexadecanoic acid
• 英文别名: (2S,3S,5R)-2-hexyl-3-hydroxy-5-((triisopropylsilyl)oxy)hexadecanoic acid；(2S,3S,5R)-2-hexyl-3-hydroxy-5-tri(propan-2-yl)silyloxyhexadecanoic acid
• CAS: 296242-38-1
• 化学式: C₃₁H₆₄O₄Si
• 分子量: 528.932
• InChiKey: PNKOWYLTAHJHOP-NGDRWEMDSA-N

物化性质

• 沸点：
  586.3±45.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.89
• 重原子数：
  36
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-2-hexyl-3-hydroxy-5-(triisopropylsilyloxy)hexadecanoic acid 在 吡啶 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 溶剂黄146 、 苯磺酰氯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 52.0h， 生成 奥利司他
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Tetrahydrolipstatin:  An anti-Aldol-Based Strategy

  摘要：

  [GRAPHICS]A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro aldol reaction to append the C2' C-11 side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.

  DOI：

  10.1021/ol000070a
• 作为产物：
  描述：

  (2S,3S,5R)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-hexadecanoic acid benzyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以99%的产率得到(2S,3S,5R)-2-hexyl-3-hydroxy-5-(triisopropylsilyloxy)hexadecanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Tetrahydrolipstatin:  An anti-Aldol-Based Strategy

  摘要：

  [GRAPHICS]A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro aldol reaction to append the C2' C-11 side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.

  DOI：

  10.1021/ol000070a

文献信息

• Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions
  作者：Arun Ghosh、Zachary Dawson

  DOI：10.1055/s-0029-1216941

  日期：2009.9

  The use of several variants of the asymmetric aldol reaction as key steps in the syntheses of bioactive target molecules is described.

  描述了使用不对称羟醛反应的几种变体作为合成生物活性靶分子的关键步骤。
• 10.1021/0l1002913
  作者：Venukadasula, Phanindra K. M.、Chegondi, Rambabu、Maitra, Soma、Hanson, Paul R.

  DOI：10.1021/0l1002913

  日期：——
• Org. Lett. 2000, 2, 2405-2407
  作者：

  DOI：——

  日期：——
• Asymmetric Synthesis of (−)-Tetrahydrolipstatin:  An <i>anti</i>-Aldol-Based Strategy
  作者：Arun K. Ghosh、Steve Fidanze

  DOI：10.1021/ol000070a

  日期：2000.8.1

  [GRAPHICS]A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro aldol reaction to append the C2' C-11 side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.