(2S,4S)-2-tert-Butoxycarbonylamino-4-methyl-5-oxo-5-pentanoylperoxy-pentanoic acid methyl ester | 592532-19-9

• 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: (2S,4S)-2-tert-Butoxycarbonylamino-4-methyl-5-oxo-5-pentanoylperoxy-pentanoic acid methyl ester
• 英文别名: methyl (2S,4S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-pentanoylperoxypentanoate
• CAS: 592532-19-9
• 化学式: C₁₇H₂₉NO₈
• 分子量: 375.419
• InChiKey: TWDRMVSXYCCAFP-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-tert-Butoxycarbonylamino-4-methyl-5-oxo-5-pentanoylperoxy-pentanoic acid methyl ester 反应 132.0h， 以34%的产率得到N-Boc-L-烯丙基甘氨酸甲酯
  参考文献：
  名称：

  Photolysis of Diacyl Peroxides:  A Radical-Based Approach for the Synthesis of Functionalized Amino Acids

  摘要：

  Photolysis of the amino acid derived symmetrical and unsymmetrical diacyl peroxides at 254 nm at low temperature (-78 to -196 degreesC) generates various bis(amino acids) in a concise manner and with orthogonal protection. The methodology was applied to the synthesis of (4R)-5-propyl-L-leucine (PrLeu), a component of HUN-7293.

  DOI：

  10.1021/ol035125y
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (2S,4S)-2-tert-Butoxycarbonylamino-4-methyl-5-oxo-5-pentanoylperoxy-pentanoic acid methyl ester
  参考文献：
  名称：

  Photolysis of Diacyl Peroxides:  A Radical-Based Approach for the Synthesis of Functionalized Amino Acids

  摘要：

  Photolysis of the amino acid derived symmetrical and unsymmetrical diacyl peroxides at 254 nm at low temperature (-78 to -196 degreesC) generates various bis(amino acids) in a concise manner and with orthogonal protection. The methodology was applied to the synthesis of (4R)-5-propyl-L-leucine (PrLeu), a component of HUN-7293.

  DOI：

  10.1021/ol035125y

文献信息

• Photolysis of Diacyl Peroxides:  A Radical-Based Approach for the Synthesis of Functionalized Amino Acids
  作者：M. Daniel Spantulescu、Rajendra P. Jain、Darren J. Derksen、John C. Vederas

  DOI：10.1021/ol035125y

  日期：2003.8.1

  Photolysis of the amino acid derived symmetrical and unsymmetrical diacyl peroxides at 254 nm at low temperature (-78 to -196 degreesC) generates various bis(amino acids) in a concise manner and with orthogonal protection. The methodology was applied to the synthesis of (4R)-5-propyl-L-leucine (PrLeu), a component of HUN-7293.