(4-{(S)-2-Acetylamino-2-[1-((S)-2-carbamoyl-1-prop-2-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester | 350584-51-9

• 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: (4-{(S)-2-Acetylamino-2-[1-((S)-2-carbamoyl-1-prop-2-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester
• 英文别名: (2S)-2-[[1-[[(2S)-2-acetamido-3-[4-[[bis[(2-methylpropan-2-yl)oxy]-oxidophosphaniumyl]methyl]phenyl]propanoyl]amino]cyclohexanecarbonyl]amino]-N-prop-2-ynylbutanediamide
• CAS: 350584-51-9
• 化学式: C₃₄H₅₂N₅O₈P
• 分子量: 689.789
• InChiKey: GSFZIGJCSWGYNP-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  201
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4-{(S)-2-Acetylamino-2-[1-((S)-2-carbamoyl-1-prop-2-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester 在 palladium on activated charcoal 、 三乙胺 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 四丁基碘化铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Convergent synthesis of potent peptide inhibitors of the Grb2-SH2 domain by palladium catalyzed coupling of a terminal alkyne

  摘要：

  A new strategy was developed to prepare in a very efficient and convergent manner C-terminal modified tripeptides with high affinities for the Grb2-SH2 domain. Using Pd(PPh3)(2)Cl-2 as catalyst, selected naphthyl iodides and triflates were coupled to Ac-Pmp(t-Bu)(2)-Ac(6)c-Asn-NH(prop-2-ynyl). The resulting alkyne derivatives were hydrogenated and deprotected to afford potent Grb2-SH2 inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00173-1
• 作为产物：
  描述：

  1-[(S)-2-Acetylamino-3-(4-chloromethyl-phenyl)-propionylamino]-cyclohexanecarboxylic acid methyl ester 在 N-甲基吗啉 、 sodium hydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (4-{(S)-2-Acetylamino-2-[1-((S)-2-carbamoyl-1-prop-2-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester
  参考文献：
  名称：

  Convergent synthesis of potent peptide inhibitors of the Grb2-SH2 domain by palladium catalyzed coupling of a terminal alkyne

  摘要：

  A new strategy was developed to prepare in a very efficient and convergent manner C-terminal modified tripeptides with high affinities for the Grb2-SH2 domain. Using Pd(PPh3)(2)Cl-2 as catalyst, selected naphthyl iodides and triflates were coupled to Ac-Pmp(t-Bu)(2)-Ac(6)c-Asn-NH(prop-2-ynyl). The resulting alkyne derivatives were hydrogenated and deprotected to afford potent Grb2-SH2 inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00173-1

文献信息

• Convergent synthesis of potent peptide inhibitors of the Grb2-SH2 domain by palladium catalyzed coupling of a terminal alkyne
  作者：Joseph Schoepfer、Brigitte Gay、Nicole End、Evelyne Muller、Gisela Scheffel、Giorgio Caravatti、Pascal Furet

  DOI：10.1016/s0960-894x(01)00173-1

  日期：2001.5

  A new strategy was developed to prepare in a very efficient and convergent manner C-terminal modified tripeptides with high affinities for the Grb2-SH2 domain. Using Pd(PPh3)(2)Cl-2 as catalyst, selected naphthyl iodides and triflates were coupled to Ac-Pmp(t-Bu)(2)-Ac(6)c-Asn-NH(prop-2-ynyl). The resulting alkyne derivatives were hydrogenated and deprotected to afford potent Grb2-SH2 inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.