2-[4-(2-Acetylamino-2-benzyloxycarbonyl-ethyl)-benzyl]-4,4-dimethoxy-3-oxo-pentanoic acid methyl ester | 182617-53-4

• 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: 2-[4-(2-Acetylamino-2-benzyloxycarbonyl-ethyl)-benzyl]-4,4-dimethoxy-3-oxo-pentanoic acid methyl ester
• CAS: 182617-53-4
• 化学式: C₂₇H₃₃NO₈
• 分子量: 499.561
• InChiKey: PEKDXLZZWBQGIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-[4-(2-Acetylamino-2-benzyloxycarbonyl-ethyl)-benzyl]-4,4-dimethoxy-3-oxo-pentanoic acid methyl ester 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 3.5h， 生成 (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{2-Acetylamino-3-[4-(3,4-dioxo-pentyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid
  参考文献：
  名称：

  α-Dicarbonyls as “non-charged” arginine-directed affinity labels. Novel synthetic routes to α-dicarbonyl analogs of the PP60c-src SH2 domain-targeted phosphopeptide Ac-Tyr(OPO3H2)-Glu-Glu-Ile-Glu

  摘要：

  The phosphopeptide 1 is a potent inhibitor of pp60(c-src) SH2 domain mediated phosphoprotein interactions (IC50 less than or equal to 0.5 mu M), hut lacks cell permeability. The syntheses of its less charged analogs 2 and 3 are described, in which the arginine-binding phosphate group has been substituted with uncharged alpha-dicarbonyl moieties. The chemistry described here may be of general use for the synthesis of other alpha-dicarbonyl compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00349-6
• 作为产物：
  描述：

  N-acetyl 4'-hydroxymethyl phenylalanine ethyl ester 在 sodium hydroxide 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 2-[4-(2-Acetylamino-2-benzyloxycarbonyl-ethyl)-benzyl]-4,4-dimethoxy-3-oxo-pentanoic acid methyl ester
  参考文献：
  名称：

  α-Dicarbonyls as “non-charged” arginine-directed affinity labels. Novel synthetic routes to α-dicarbonyl analogs of the PP60c-src SH2 domain-targeted phosphopeptide Ac-Tyr(OPO3H2)-Glu-Glu-Ile-Glu

  摘要：

  The phosphopeptide 1 is a potent inhibitor of pp60(c-src) SH2 domain mediated phosphoprotein interactions (IC50 less than or equal to 0.5 mu M), hut lacks cell permeability. The syntheses of its less charged analogs 2 and 3 are described, in which the arginine-binding phosphate group has been substituted with uncharged alpha-dicarbonyl moieties. The chemistry described here may be of general use for the synthesis of other alpha-dicarbonyl compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00349-6