2-((4S,13S)-13-Benzyloxycarbonylamino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid ethyl ester | 474686-26-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 2-((4S,13S)-13-Benzyloxycarbonylamino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2-[(4S,13S)-2,7-dioxo-13-(phenylmethoxycarbonylamino)-15-oxa-3,8,17-triazabicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl]-1,3-thiazole-4-carboxylate
• CAS: 474686-26-5
• 化学式: C₂₇H₃₁N₅O₇S
• 分子量: 569.638
• InChiKey: XQOQTYLICMGCBF-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  190
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-((4S,13S)-13-Benzyloxycarbonylamino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid ethyl ester 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 生成 2-((4S,13S)-13-Benzyloxycarbonylamino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Regioselective Synthesis of Antiparallel Loops on a Macrocyclic Scaffold Constrained by Oxazoles and Thiazoles

  摘要：

  [GRAPHICS]The regioselective syntheses and structures are reported for two tris-macrocylic compounds, each possessing two antiparallel loops on a macrocyclic scaffold constrained by two oxazoles and two thiazoles. NMR solution structures show the loops projecting from the same face of the macrocycle. Such molecules are shown to be prototypes for mimicking multiple loops of proteins.

  DOI：

  10.1021/ol026463m
• 作为产物：
  描述：

  2-((S)-1-{[2-((S)-5-Amino-1-benzyloxycarbonylamino-pentyl)-oxazole-4-carbonyl]-amino}-3-carboxy-propyl)-thiazole-4-carboxylic acid ethyl ester; compound with trifluoro-acetic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以91%的产率得到2-((4S,13S)-13-Benzyloxycarbonylamino-2,7-dioxo-15-oxa-3,8,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-thiazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Regioselective Synthesis of Antiparallel Loops on a Macrocyclic Scaffold Constrained by Oxazoles and Thiazoles

  摘要：

  [GRAPHICS]The regioselective syntheses and structures are reported for two tris-macrocylic compounds, each possessing two antiparallel loops on a macrocyclic scaffold constrained by two oxazoles and two thiazoles. NMR solution structures show the loops projecting from the same face of the macrocycle. Such molecules are shown to be prototypes for mimicking multiple loops of proteins.

  DOI：

  10.1021/ol026463m