methyl (4R)-4-acetamido-2-oxo-5-phenylpentanoate | 873088-00-7

• 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: methyl (4R)-4-acetamido-2-oxo-5-phenylpentanoate
• CAS: 873088-00-7
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: RSNFZVJJHUIQFK-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-acetamido-2-oxo-5-phenylpentanoate 在 sodium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 生成 (S)-4-((R)-3-Acetylamino-4-phenyl-butyrylamino)-5-methyl-2-oxo-hexanoic acid methyl ester
  参考文献：
  名称：

  Iterative, Aqueous Synthesis of β³-Oligopeptides without Coupling Reagents

  摘要：

  The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.

  DOI：

  10.1021/ja057706j
• 作为产物：
  描述：

  methyl (3R)-3-benzyl-5-methoxy-1,2-oxazolidine-5-carboxylate 、 丙酮酸 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以93%的产率得到methyl (4R)-4-acetamido-2-oxo-5-phenylpentanoate
  参考文献：
  名称：

  Iterative, Aqueous Synthesis of β³-Oligopeptides without Coupling Reagents

  摘要：

  The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.

  DOI：

  10.1021/ja057706j

文献信息

• Iterative, Aqueous Synthesis of β³-Oligopeptides without Coupling Reagents
  作者：Nancy Carrillo、Eric A. Davalos、Justin A. Russak、Jeffrey W. Bode

  DOI：10.1021/ja057706j

  日期：2006.2.1

  The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.