N-t-butoxycarbonyl-(S)-O-benzyltyrosyl-(S)-proline methyl ester | 140685-07-0

• 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-t-butoxycarbonyl-(S)-O-benzyltyrosyl-(S)-proline methyl ester
• 英文别名: methyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylmethoxyphenyl)propanoyl]pyrrolidine-2-carboxylate
• CAS: 140685-07-0
• 化学式: C₂₇H₃₄N₂O₆
• 分子量: 482.577
• InChiKey: MLBMNOSDWXZHJR-GOTSBHOMSA-N

物化性质

• 沸点：
  654.0±55.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-t-butoxycarbonyl-(S)-O-benzyltyrosyl-(S)-proline methyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Degradation of Azaglycinamido Residues in Model Tripeptides Derived from Goserelin

  摘要：

  Three model tripeptides, N-acetyl-Tyr-Pro-azaGly-NH2 (NYPaG), Tyr-Pro-azaGly-NH2 (YPaG), and Tyr-Pro-Gly-NH2(YPG), were subjected to a systematic degradation study to get information about the degradation of the azaglycinamido residue. The degradation products were characterized with LC-MS. Main degradation products of NYPaG possess partially or totally eliminated azaglycinamido residues, while YPaG and YPG are exhibit cyclo(Tyr-Pro) formation, a diketopiperazine. The influence of the pH on the degradation rate constant k(obs) was investigated for NYPaG and YPaG in the pH range 0.4-11. An U-shaped profile with an inflexion around pH 9 was found for NYPaG while the degradation rate of YPaG was independent of the pH. NYPaG apparently was subject to proton-, solvent-, and hydroxyl-catalyzed degradation reactions whereas YPaG only underwent solvent-catalyzed reactions. Some influence of acetate and phosphate ions on k(obs) was found fur YPaG. Arrhenius plots of NYPaG and YPaG; were found to be linear. (C) 2000 Wiley-Liss, Inc. and the American Pharmaceutical Association.

  DOI：

  10.1002/(sici)1520-6017(200001)89:1<108::aid-jps11>3.0.co;2-a
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 、 L-脯氨酸甲酯盐酸盐 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 以96%的产率得到N-t-butoxycarbonyl-(S)-O-benzyltyrosyl-(S)-proline methyl ester
  参考文献：
  名称：

  Schoen, I.; Szirtes, T.; Rill, A., Acta Chimica Hungarica, 1991, vol. 128, # 6, p. 751 - 773

  摘要：

  DOI：

文献信息

• Selective BH3-Reduction of Amide Carbonyl Groups of Lithium Salts of N-t-Butoxycarbonyl (S)-O-Benzyl Tyrosyl (S)-Proline and N,N′-Ethylene-Bridged Dipeptides
  作者：Kenichi Adachi、Eiji Tsuru、Eri Banjyo、Matsumi Doe、Kozo Shibata、Tetsushi Yamashita

  DOI：10.1055/s-1998-2192

  日期：1998.11