N-(N-benzyloxycarbonyl-D-phenylalanyl)-p-bis(2-chloroethyl)amino-L-phenylalanine benzyl ester | 223431-93-4

• 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: N-(N-benzyloxycarbonyl-D-phenylalanyl)-p-bis(2-chloroethyl)amino-L-phenylalanine benzyl ester
• 英文别名: benzyl (2S)-3-[4-[bis(2-chloroethyl)amino]phenyl]-2-[[(2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 223431-93-4
• 化学式: C₃₇H₃₉Cl₂N₃O₅
• 分子量: 676.64
• InChiKey: DBQCLPVSAMTKIG-NOCHOARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  草酸 、 N-(N-benzyloxycarbonyl-D-phenylalanyl)-p-bis(2-chloroethyl)amino-L-phenylalanine benzyl ester 在 palladium on activated charcoal 水 、 氢气 作用下， 以 甲醇 为溶剂， 以62%的产率得到D-phenylalanylmelphalan
  参考文献：
  名称：

  Synthesis of ?-aminoacyl derivatives of melphalan for use in antibody directed enzyme pro-drug therapy

  摘要：

  L-Alanyl-, D-alanyl-, L-prolyl-, L-pyroglutamyl- and D-phenylalanylmelphalan were synthesized in 8 steps, with the reactive nitrogen mustard moiety formed at the penultimate step. After protection of p-nitrophenylalanine with benzyl ester and N-t-butyloxycarbonyl (BOC) groups, the aromatic nitro was reduced to an amine which was reacted with ethylene oxide to give a product with a bis(2-hydroxyethyl)amino moiety. After removal of BOC, it was coupled to the relevant N-benzyloxycarbonyl-alpha-amino acid. Chlorination of hydroxyethyl yielded the bis(2-chlorethyl)amino compound. Final removal of protecting groups was by catalytic hydrogenolysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01139-9
• 作为产物：
  描述：

  p-amino-N-tert-butyloxycarbonyl-L-phenylalanine benzyl ester 在 盐酸 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 29.0h， 生成 N-(N-benzyloxycarbonyl-D-phenylalanyl)-p-bis(2-chloroethyl)amino-L-phenylalanine benzyl ester
  参考文献：
  名称：

  Synthesis of ?-aminoacyl derivatives of melphalan for use in antibody directed enzyme pro-drug therapy

  摘要：

  L-Alanyl-, D-alanyl-, L-prolyl-, L-pyroglutamyl- and D-phenylalanylmelphalan were synthesized in 8 steps, with the reactive nitrogen mustard moiety formed at the penultimate step. After protection of p-nitrophenylalanine with benzyl ester and N-t-butyloxycarbonyl (BOC) groups, the aromatic nitro was reduced to an amine which was reacted with ethylene oxide to give a product with a bis(2-hydroxyethyl)amino moiety. After removal of BOC, it was coupled to the relevant N-benzyloxycarbonyl-alpha-amino acid. Chlorination of hydroxyethyl yielded the bis(2-chlorethyl)amino compound. Final removal of protecting groups was by catalytic hydrogenolysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01139-9