N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline | 445396-44-1

• 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: N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline
• 英文别名: Z-Phe-D/L-Iva-Pro-OH
• CAS: 445396-44-1
• 化学式: C₂₇H₃₃N₃O₆
• 分子量: 495.576
• InChiKey: BMLQNTIFAGDYEO-BTOHDXCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  125.04
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-酞酰亚胺基丙酸甲酯 、 N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以82%的产率得到methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-prolyl-(S)-alaninate
  参考文献：
  名称：

  Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons

  摘要：

  The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx = alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.

  DOI：

  10.1002/1522-2675(200203)85:3<885::aid-hlca885>3.0.co;2-z
• 作为产物：
  描述：

  methyl (S)-N-(1-chloro-2-methylbut-1-enyl)prolinate 在 lithium hydroxide 、 sodium azide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 26.0h， 生成 N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-(R/S)-methyl(ethyl)glycyl-(S)-proline
  参考文献：
  名称：

  Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons

  摘要：

  The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx = alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.

  DOI：

  10.1002/1522-2675(200203)85:3<885::aid-hlca885>3.0.co;2-z