Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate | 152906-21-3

• 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: Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate
• 英文别名: methyl (2S,3S,5R)-2-hexyl-3-hydroxy-5-phenylmethoxyhexadecanoate
• CAS: 152906-21-3
• 化学式: C₃₀H₅₂O₄
• 分子量: 476.74
• InChiKey: HJUBAKRPMASVBJ-ULNSLHSMSA-N

物化性质

• 沸点：
  570.7±40.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  34
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 、 苯磺酰氯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 奥利司他
  参考文献：
  名称：

  Total synthesis of (-)-tetrahydrolipstatin

  摘要：

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.

  DOI：

  10.1021/jo00079a022
• 作为产物：
  描述：

  (R)-3-(benzyloxy)tetradecanal 在 四氯化钛 silver trifluoromethanesulfonate 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 8.08h， 生成 Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate
  参考文献：
  名称：

  Total synthesis of (-)-tetrahydrolipstatin

  摘要：

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.

  DOI：

  10.1021/jo00079a022