methyl (5S,8S,11S)-11-benzyl-8-(4-((tert-butoxycarbonyl)amino)butyl)-7,10,13-trioxo-2-oxa-6,9,12-triaza-1(2,4)-pyridina-3(1,4)-benzenacyclotridecaphane-5-carboxylate | 1374840-53-5

• 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: methyl (5S,8S,11S)-11-benzyl-8-(4-((tert-butoxycarbonyl)amino)butyl)-7,10,13-trioxo-2-oxa-6,9,12-triaza-1(2,4)-pyridina-3(1,4)-benzenacyclotridecaphane-5-carboxylate
• CAS: 1374840-53-5
• 化学式: C₃₆H₄₃N₅O₈
• 分子量: 673.766
• InChiKey: HBHQQSKTIODMQH-AWCRTANDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  49.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  174.05
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4-(((S)-1-(((4S,7S)-4-(4-hydroxybenzyl)-15,15-dimethyl-3,6,13-trioxo-2,14-dioxa-5,12-diazahexadecan-7-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamoyl)pyridine 1-oxide 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到methyl (5S,8S,11S)-11-benzyl-8-(4-((tert-butoxycarbonyl)amino)butyl)-7,10,13-trioxo-2-oxa-6,9,12-triaza-1(2,4)-pyridina-3(1,4)-benzenacyclotridecaphane-5-carboxylate
  参考文献：
  名称：

  A New and Useful Method for the Macrocyclization of Linear Peptides

  摘要：

  A new and useful procedure for the macrocyclization of linear peptides is described. The natural amino acid side chains of tyrosine (phenol), lysine (alkylamine), and histidine (imidazole) react in an Intramolecular fashion with a pendent pyridine-N-oxide-carboxamide, which is selectively activated by the phosphonium salt, PyBroP. The reaction is mild, rapid, and efficient with a potentially large substrate scope. Multiple examples are provided with full characterization and analyses, including a novel aza-variant of the C-O-D ring system of vancomycin.

  DOI：

  10.1021/ol301173m