(2S,3S,5R)-5-(Benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid | 153064-98-3

• 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: (2S,3S,5R)-5-(Benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid
• 英文别名: (2R,3S,5R)-2-hexyl-3-hydroxy-5-phenylmethoxyhexadecanoic acid
• CAS: 153064-98-3
• 化学式: C₂₉H₅₀O₄
• 分子量: 462.714
• InChiKey: NYMBAVXCWMVOCP-FCEKVYKBSA-N

物化性质

• 沸点：
  598.4±45.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  33
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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)-5-(Benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid 在 palladium on activated charcoal 吡啶 、 氢气 、 苯磺酰氯 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 0.33h， 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：

  (2R,3S,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hexyl-hexadecanal 在 sodium chlorite 、 Na₂H₂PO₄*H₂O 、 氢氟酸 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 8.5h， 生成 (2S,3S,5R)-5-(Benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid
  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

文献信息

• METHOD FOR PREPARING (3S,4S)-4-((R)-2-(BENZYLOXY)TRIDECYL)-3-HEXYL-2-OXETANONE AND NOVEL INTERMEDIATE USED THEREFOR
  申请人：Yun Sang Min

  公开号：US20110178330A1

  公开（公告）日：2011-07-21

  The present invention relates to a high-yield method for preparing highly pure (3S,4S)-4-((R)-2-(benzyloxy)tridecyl)-3-hexyl-2-oxetanone using a metal salt of (2S,3S,5R)-2-hexyl-3,5-dihydroxyhexadecanoic acid as an intermediate.

  本发明涉及一种高产纯度的方法，用(2S,3S,5R)-2-己基-3,5-二羟基十六酸的金属盐作为中间体，制备高纯度的(3S,4S)-4-((R)-2-(苄氧)十三烷基)-3-己基-2-氧杂环戊酮。
• US8637700B2
  申请人：——

  公开号：US8637700B2

  公开（公告）日：2014-01-28