(S)-N^α-phthaloyl-O-benzyltyrosinylglycine | 306775-45-1

• 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)-N^α-phthaloyl-O-benzyltyrosinylglycine
• 英文别名: Pht-Tyr(Bzl)-Gly-OH；2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-(4-phenylmethoxyphenyl)propanoyl]amino]acetic acid
• CAS: 306775-45-1
• 化学式: C₂₆H₂₂N₂O₆
• 分子量: 458.47
• InChiKey: ALDPEIOHUMMWNE-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N^α-phthaloyl-O-benzyltyrosinylglycine 在 三氟甲磺酸 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 4(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1,3,4,5-tetrahydro-80hydroxy-3-oxo-2Hbenzazepin-2-acetic acid
  参考文献：
  名称：

  Synthesis of a conformationally constrained tyrosine–glycine dipeptide mimetic: design of a potential substrate of Syk kinase

  摘要：

  The synthesis of a conformationally restricted tyrosine-glycine dipeptide mimetic and its insertion into an octapeptide is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00635-4
• 作为产物：
  描述：

  [(S)-3-(4-Benzyloxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionylamino]-acetic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(S)-N^α-phthaloyl-O-benzyltyrosinylglycine
  参考文献：
  名称：

  Synthesis of a conformationally constrained tyrosine–glycine dipeptide mimetic: design of a potential substrate of Syk kinase

  摘要：

  The synthesis of a conformationally restricted tyrosine-glycine dipeptide mimetic and its insertion into an octapeptide is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00635-4

文献信息

• Efficient Synthesis of (<i>S</i>)-4-Phthalimido-1,3,4,5- tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2<i>H</i>-2-benzazepin-2-acetic Acid (Pht-Hba(2,6-Cl₂-Bn)-Gly-OH)¹
  作者：J. Richard Casimir、Dirk Tourwé、Koen Iterbeke、Gilles Guichard、Jean-Paul Briand

  DOI：10.1021/jo000530d

  日期：2000.10.1

  4-Amino-2-benzazepin-3-ones have proven very useful for studying the biologically active conformations of peptides. The synthesis of Pht-Aba-Xaa-OH by reaction of the corresponding 1,3-oxazolidin-5-one with trifluoromethanesulfonic acid (TFMSA) has been reported in the literature. However, when this procedure was applied to the preparation of Pht-Hba(Bn)-Gly-OH 8, many byproducts were formed and the yield of the desired aminobenzazepinones 7 and 8 was very low. We report in this paper an efficient methodology for the synthesis of Pht-Hba(2,6-Cl-2-Bn)-Gly-OH 17 starting from the commercially available tyro sine. In our procedure, the dipeptide Pht-Tyr(2,6-Cl-2-Bn)-Gly-OH 15 is converted,to the 1,3-oxazolidin-5-one 16 Which then undergoes Friedel-Crafts cyclization in the presence of tin tetrachloride to afford the desired 4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-2-benzazepin-3-one 17 in excellent yield.
• Synthesis of a conformationally constrained tyrosine–glycine dipeptide mimetic: design of a potential substrate of Syk kinase
  作者：Paolo Ruzza、Andrea Calderan、Alessio Osler、Stefano Elardo、Gianfranco Borin

  DOI：10.1016/s0040-4039(02)00635-4

  日期：2002.5

  The synthesis of a conformationally restricted tyrosine-glycine dipeptide mimetic and its insertion into an octapeptide is described. (C) 2002 Elsevier Science Ltd. All rights reserved.