isopropyl (2S,3S)-5-diazo-3-methyl-4-oxo-2-[(trifluoroacetyl)amino]pentanoate | 160006-14-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: isopropyl (2S,3S)-5-diazo-3-methyl-4-oxo-2-[(trifluoroacetyl)amino]pentanoate
• 英文别名: 1-isopropyl (2S,3S)-5-diazo-4-oxo-N-trifluoroacetylisoleucinate；isopropyl 5-diazo-4-oxo-N-(trifluoroacetyl)-L-alloisoleucinate；propan-2-yl (2S,3S)-5-diazo-3-methyl-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]pentanoate
• CAS: 160006-14-4
• 化学式: C₁₁H₁₄F₃N₃O₄
• 分子量: 309.245
• InChiKey: LMADKLVBDVKPTL-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl (2S,3S)-5-diazo-3-methyl-4-oxo-2-[(trifluoroacetyl)amino]pentanoate 在 盐酸 、 silver benzoate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (2S,3R)-3-methylglutamic acid
  参考文献：
  名称：

  Callipeltins J–M的分离和结构解析：来自海洋海绵Latrunculia sp。的抗真菌肽。

  摘要：

  继续研究海洋海绵Latrunculia sp。的极性提取物。已经导致发现卡培尔丁J–M。通过解释其NMR和MS数据确定新结构。立体选择性合成和Marfey的LC-MS分析确保了愈伤组织J和K中不常见的3-甲基谷氨酰胺残基的立体化学。

  DOI：

  10.1016/j.tet.2006.10.032
• 作为产物：
  描述：

  (+/-)-threo-3-methylaspartic acid 在 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.67h， 生成 isopropyl (2S,3S)-5-diazo-3-methyl-4-oxo-2-[(trifluoroacetyl)amino]pentanoate
  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.
• Isolation and structural elucidation of callipeltins J–M: antifungal peptides from the marine sponge Latrunculia sp.
  作者：Maria Valeria D'Auria、Valentina Sepe、Rosa D'Orsi、Filomena Bellotta、Cécile Debitus、Angela Zampella

  DOI：10.1016/j.tet.2006.10.032

  日期：2007.1

  Continued investigation of the polar extracts of the marine sponge Latrunculia sp. has resulted in the discovery of callipeltins J–M. The new structures were determined by interpretation of their NMR and MS data. The stereochemistry of the unusual 3-methylglutamine residue in callipeltins J and K was secured by stereoselective synthesis and Marfey's LC–MS analysis.

  继续研究海洋海绵Latrunculia sp。的极性提取物。已经导致发现卡培尔丁J–M。通过解释其NMR和MS数据确定新结构。立体选择性合成和Marfey的LC-MS分析确保了愈伤组织J和K中不常见的3-甲基谷氨酰胺残基的立体化学。