N-benzyloxycarbonyl-O-benzyl-(Z)dehydrotyrosine ethyl ester | 145763-44-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-benzyloxycarbonyl-O-benzyl-(Z)dehydrotyrosine ethyl ester
• CAS: 145763-44-6
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: KEVZTLLXOYSYLK-ULJHMMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-benzyl-(Z)dehydrotyrosine ethyl ester 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以68%的产率得到N-benzyloxycarbonyl-O-benzyl-(Z)dehydrotyrosine
  参考文献：
  名称：

  Diastereoselective hydrogenation of monodehydro enkephalins controlled by chiral rhodium catalysts

  摘要：

  Protected (Z)dehydrophenylalanyl-Leu-enkephalin, (Z)dehydrotyrosyl-Leu-enkephalin and (Z)dehydrotyrosyl-(R)Ala2-Leu-enkephalin, have been synthesized. These compounds have been hydrogenated to give protected Leu-enkephalins in the presence of various chiral rhodium complexes. Deprotection of the product gave Leu-enkephalins or epimers, ytterbium in liquid ammonia allows smooth deprotection of NHCBz or OTs groups on small amounts of peptides. Strong stereocontrol could be achieved by suitable choice of the chiral catalyst. This method has good potential for stereospecific labelling of enkephalins and other small peptides.

  DOI：

  10.1016/s0957-4166(00)82083-2
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 2-Benzyloxycarbonylamino-2-diethyloxyphosphoryl-essigsaeure-ethylester 在 potassium tert-butylate 作用下， 生成 N-benzyloxycarbonyl-O-benzyl-(Z)dehydrotyrosine ethyl ester
  参考文献：
  名称：

  Diastereoselective hydrogenation of monodehydro enkephalins controlled by chiral rhodium catalysts

  摘要：

  Protected (Z)dehydrophenylalanyl-Leu-enkephalin, (Z)dehydrotyrosyl-Leu-enkephalin and (Z)dehydrotyrosyl-(R)Ala2-Leu-enkephalin, have been synthesized. These compounds have been hydrogenated to give protected Leu-enkephalins in the presence of various chiral rhodium complexes. Deprotection of the product gave Leu-enkephalins or epimers, ytterbium in liquid ammonia allows smooth deprotection of NHCBz or OTs groups on small amounts of peptides. Strong stereocontrol could be achieved by suitable choice of the chiral catalyst. This method has good potential for stereospecific labelling of enkephalins and other small peptides.

  DOI：

  10.1016/s0957-4166(00)82083-2