(S)-2-((tert-butoxycarbonyl)amino)-4-(4-methoxyphenyl)-4-oxobutanoic acid | 174464-17-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-((tert-butoxycarbonyl)amino)-4-(4-methoxyphenyl)-4-oxobutanoic acid
• 英文别名: (2S)-4-(4-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid
• CAS: 174464-17-6
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: FEMJHMIOAACJOU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-((tert-butoxycarbonyl)amino)-4-(4-methoxyphenyl)-4-oxobutanoic acid 在 N-甲基吗啉 、 N-甲基咪唑 、 甲醇 、 1,1'-carbonylbis(3-methylimidazolium) triflate 、 乙酰氯 、 N,N'-羰基二咪唑 、 三氟甲烷磺酸甲酯 作用下， 以 乙酸乙酯 为溶剂， 反应 5.72h， 生成 BOC-Met-An^pAsp-Ile-OCH3
  参考文献：
  名称：

  Synthesis of Anisolylated Aspartyl and Glutamyl Tripeptides

  摘要：

  A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation-the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.

  DOI：

  10.1021/jo951754c
• 作为产物：
  描述：

  tert-butyl (S)-2-((tert-butoxycarbonyl)amino)-4-(4-methoxyphenyl)-4-oxobutanoate 在 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 (S)-2-((tert-butoxycarbonyl)amino)-4-(4-methoxyphenyl)-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis of Anisolylated Aspartyl and Glutamyl Tripeptides

  摘要：

  A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation-the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.

  DOI：

  10.1021/jo951754c

文献信息

• Synthesis of Anisolylated Aspartyl and Glutamyl Tripeptides
  作者：Fabienne Berrée、Kieyoung Chang、Agustín Cobas、Henry Rapoport

  DOI：10.1021/jo951754c

  日期：1996.1.1

  A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation-the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.