isopentyl (3R,2'S,5'R)-3-<5'-isopropyl-3',6'-dimethoxy-2',5'-dihydropyrazin-2'-yl>butanoate | 160006-16-6

• 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: isopentyl (3R,2'S,5'R)-3-<5'-isopropyl-3',6'-dimethoxy-2',5'-dihydropyrazin-2'-yl>butanoate
• 英文别名: 3-methylbutyl (3R)-3-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]butanoate
• CAS: 160006-16-6
• 化学式: C₁₈H₃₂N₂O₄
• 分子量: 340.463
• InChiKey: WNSLFAYPCLCRPS-BMFZPTHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isopentyl (3R,2'S,5'R)-3-<5'-isopropyl-3',6'-dimethoxy-2',5'-dihydropyrazin-2'-yl>butanoate 在 盐酸 作用下， 反应 2.0h， 以42%的产率得到(2S,3R)-3-methylglutamic acid
  参考文献：
  名称：

  Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid

  摘要：

  Arndt-Eistert homologation of suitably-protected (2S,3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S,3R)-3-methylglutamic acid. (2S,3R)-3- Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether. of cyclo-(R-Val-Gly) to methyl (E)-butenoate. The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S,3S)-3-methylglutamic acid. Both conjugate additions occurred with high diastereoselectivity.

  DOI：

  10.1039/p19940002525
• 作为产物：
  描述：

  isopentyl but-2-ynoate 在 palladium on barium sulfate 正丁基锂 、 氢气 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 反应 7.25h， 生成 isopentyl (3R,2'S,5'R)-3-<5'-isopropyl-3',6'-dimethoxy-2',5'-dihydropyrazin-2'-yl>butanoate
  参考文献：
  名称：

  Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid

  摘要：

  Arndt-Eistert homologation of suitably-protected (2S,3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S,3R)-3-methylglutamic acid. (2S,3R)-3- Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether. of cyclo-(R-Val-Gly) to methyl (E)-butenoate. The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S,3S)-3-methylglutamic acid. Both conjugate additions occurred with high diastereoselectivity.

  DOI：

  10.1039/p19940002525

文献信息

• Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid
  作者：Basil Hartzoulakis、David Gani

  DOI：10.1039/p19940002525

  日期：——

  Arndt-Eistert homologation of suitably-protected (2S,3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S,3R)-3-methylglutamic acid. (2S,3R)-3- Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether. of cyclo-(R-Val-Gly) to methyl (E)-butenoate. The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S,3S)-3-methylglutamic acid. Both conjugate additions occurred with high diastereoselectivity.