benzoinyl N-carbobenzyloxyglycylphenylalanate

• 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: benzoinyl N-carbobenzyloxyglycylphenylalanate
• 英文别名: (2-oxo-1,2-diphenylethyl) (2S)-3-phenyl-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoate
• 化学式: C₃₃H₃₀N₂O₆
• 分子量: 550.611
• InChiKey: XYWVHABDRTWOPG-NPHAVVRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzoinyl N-carbobenzyloxyglycylphenylalanate 以 甲醇 为溶剂， 反应 0.17h， 生成 2-苯基-1-苯并呋喃
  参考文献：
  名称：

  Photolabile benzoin and furoin esters of a biologically active peptide

  摘要：

  Benzoin and furoin esters of N-carbobenzyloxyglycylphenylalanine were prepared and photolyzed under a variety of conditions. The photochemistry of peptide-derived benzoin esters is more efficient than that of furoin esters and is appropriate for the photolytic initiation of biochemical processes. Methodology to assess the enantiomeric purity of the resulting free peptide was developed and used to monitor the protection-deprotection chemistry. Synthesis based on alkylation of the cesium salt of the peptide proved more effective than DCCI-mediated chemistry on stereochemical grounds.

  DOI：

  10.1016/0040-4020(95)00573-q
• 作为产物：
  描述：

  N-苄氧羰基甘氨酰-L-苯丙氨酸 、 安息香精油 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以63%的产率得到benzoinyl N-carbobenzyloxyglycylphenylalanate
  参考文献：
  名称：

  Photolabile benzoin and furoin esters of a biologically active peptide

  摘要：

  Benzoin and furoin esters of N-carbobenzyloxyglycylphenylalanine were prepared and photolyzed under a variety of conditions. The photochemistry of peptide-derived benzoin esters is more efficient than that of furoin esters and is appropriate for the photolytic initiation of biochemical processes. Methodology to assess the enantiomeric purity of the resulting free peptide was developed and used to monitor the protection-deprotection chemistry. Synthesis based on alkylation of the cesium salt of the peptide proved more effective than DCCI-mediated chemistry on stereochemical grounds.

  DOI：

  10.1016/0040-4020(95)00573-q

文献信息

• Photolabile benzoin and furoin esters of a biologically active peptide
  作者：Josephine M. Peach、Andrew J. Pratt、John S. Snaith

  DOI：10.1016/0040-4020(95)00573-q

  日期：1995.1

  Benzoin and furoin esters of N-carbobenzyloxyglycylphenylalanine were prepared and photolyzed under a variety of conditions. The photochemistry of peptide-derived benzoin esters is more efficient than that of furoin esters and is appropriate for the photolytic initiation of biochemical processes. Methodology to assess the enantiomeric purity of the resulting free peptide was developed and used to monitor the protection-deprotection chemistry. Synthesis based on alkylation of the cesium salt of the peptide proved more effective than DCCI-mediated chemistry on stereochemical grounds.