(1S,4S,5S,8S,14S)-8-benzyl-14-isobutyl-4-methyl-3,7,10,13,16-pentaazatricyclo[14.2.0.03,5]octadecane-2,6,9,12,15-pentaone | 1569904-16-0

• 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: (1S,4S,5S,8S,14S)-8-benzyl-14-isobutyl-4-methyl-3,7,10,13,16-pentaazatricyclo[14.2.0.03,5]octadecane-2,6,9,12,15-pentaone
• CAS: 1569904-16-0
• 化学式: C₂₅H₃₃N₅O₅
• 分子量: 483.568
• InChiKey: RNPGAZUSFJIFSD-URMPPTTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.43
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  127.69
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-羟基-7-氮杂苯并三氮唑 、 (1S,4S,5S,8S,14S)-8-benzyl-14-isobutyl-4-methyl-3,7,10,13,16-pentaazatricyclo[14.2.0.03,5]octadecane-2,6,9,12,15-pentaone 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以2.1 mg的产率得到(3S,9S,12R,13S,16S)-12-azido-9-benzyl-3-isobutyl-13-methyl-1,4,7,10,14-pentaazabicyclo[14.2.0]octadecane-2,5,8,11,15-pentaone
  参考文献：
  名称：

  Site-Specific Integration of Amino Acid Fragments into Cyclic Peptides

  摘要：

  The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.

  DOI：

  10.1021/ja412256f
• 作为产物：
  描述：

  methyl (S)-1-(((2S,3S)-3-methylaziridine-2-carbonyl)-L-phenylalanylglycyl-L-leucyl)azetidine-2-carboxylate 在 N,N-二异丙基乙胺 、 (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium hexafluoro-lambda5-phosphanuide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到(1S,4S,5S,8S,14S)-8-benzyl-14-isobutyl-4-methyl-3,7,10,13,16-pentaazatricyclo[14.2.0.03,5]octadecane-2,6,9,12,15-pentaone
  参考文献：
  名称：

  Site-Specific Integration of Amino Acid Fragments into Cyclic Peptides

  摘要：

  The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.

  DOI：

  10.1021/ja412256f