(S)-4-{(S)-2-Benzoylamino-3-[4-(di-tert-butoxy-phosphoryloxy)-phenyl]-propionylamino}-4-dipentylcarbamoyl-butyric acid tert-butyl ester | 205236-47-1

• 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: (S)-4-{(S)-2-Benzoylamino-3-[4-(di-tert-butoxy-phosphoryloxy)-phenyl]-propionylamino}-4-dipentylcarbamoyl-butyric acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[[(2S)-2-benzamido-3-[4-[bis[(2-methylpropan-2-yl)oxy]phosphoryloxy]phenyl]propanoyl]amino]-5-(dipentylamino)-5-oxopentanoate
• CAS: 205236-47-1
• 化学式: C₄₃H₆₈N₃O₉P
• 分子量: 802.001
• InChiKey: OLINDYAPOUKLRL-ZPGRZCPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  56
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-4-{(S)-2-Benzoylamino-3-[4-(di-tert-butoxy-phosphoryloxy)-phenyl]-propionylamino}-4-dipentylcarbamoyl-butyric acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到(S)-4-[(S)-2-Benzoylamino-3-(4-phosphonooxy-phenyl)-propionylamino]-4-dipentylcarbamoyl-butyric acid
  参考文献：
  名称：

  Potent Dipeptide Inhibitors of the pp60^c-src SH2 Domain

  摘要：

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.

  DOI：

  10.1021/jm970853a
• 作为产物：
  描述：

  N-苄氧羰基-L-谷氨酸γ-叔丁酯 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 sodium hydride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 41.58h， 生成 (S)-4-{(S)-2-Benzoylamino-3-[4-(di-tert-butoxy-phosphoryloxy)-phenyl]-propionylamino}-4-dipentylcarbamoyl-butyric acid tert-butyl ester
  参考文献：
  名称：

  Potent Dipeptide Inhibitors of the pp60^c-src SH2 Domain

  摘要：

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.

  DOI：

  10.1021/jm970853a