benzyl N-(tert-butoxycarbonyl)-3-{5-[((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylamino)methyl]-1H-1,2,3-triazol-1-yl}-L-alaninate | 1346521-93-4

• 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: benzyl N-(tert-butoxycarbonyl)-3-{5-[((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylamino)methyl]-1H-1,2,3-triazol-1-yl}-L-alaninate
• CAS: 1346521-93-4
• 化学式: C₂₈H₃₅N₅O₆
• 分子量: 537.616
• InChiKey: CWVCCKYUTCBBTB-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  133.67
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl N-(tert-butoxycarbonyl)-3-{5-[((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylamino)methyl]-1H-1,2,3-triazol-1-yl}-L-alaninate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 反应 1.5h， 以87%的产率得到N-(tert-butoxycarbonyl)-3-{5-[((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylamino)methyl]-1H-1,2,3-triazol-1-yl}-L-alanine
  参考文献：
  名称：

  Amino Triazolo Diazepines (Ata) as Constrained Histidine Mimics

  摘要：

  Two synthetic routes for the synthesis of amino-triazolodiazepine (Ata) scaffolds are presented. The scope of both of these proceeding through key intra- and intermolecular Huisgen cycloaddition reactions is discussed. The replacement of the His-Pro dipeptide segment in angiotensin IV by the dipeptide mimetic Ata-Gly and subsequent biological evaluation in two inhibitory enzyme assays validated the use of the Ata moiety as a His mimic given the equipotency of both peptidic analogs.

  DOI：

  10.1021/ol202767k
• 作为产物：
  描述：

  benzyl (2S)-3-azido-2-[(tert-butoxycarbonyl)amino]propanoate 、 methyl N-(2-propynyl)-S-phenylalaninate 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以94%的产率得到benzyl N-(tert-butoxycarbonyl)-3-{5-[((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylamino)methyl]-1H-1,2,3-triazol-1-yl}-L-alaninate
  参考文献：
  名称：

  Amino Triazolo Diazepines (Ata) as Constrained Histidine Mimics

  摘要：

  Two synthetic routes for the synthesis of amino-triazolodiazepine (Ata) scaffolds are presented. The scope of both of these proceeding through key intra- and intermolecular Huisgen cycloaddition reactions is discussed. The replacement of the His-Pro dipeptide segment in angiotensin IV by the dipeptide mimetic Ata-Gly and subsequent biological evaluation in two inhibitory enzyme assays validated the use of the Ata moiety as a His mimic given the equipotency of both peptidic analogs.

  DOI：

  10.1021/ol202767k