benzyl ((S)-6-azido-1-(((S)-1-(((S)-1-hydroxy-3-(4-(prop-2-yn-1-yloxy)phenyl)propan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxohexan-2-yl)carbamate | 1359969-79-1

• 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: benzyl ((S)-6-azido-1-(((S)-1-(((S)-1-hydroxy-3-(4-(prop-2-yn-1-yloxy)phenyl)propan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxohexan-2-yl)carbamate
• CAS: 1359969-79-1
• 化学式: C₃₂H₄₂N₆O₆
• 分子量: 606.722
• InChiKey: SKKMTVUTRFBTMH-ZXRKZBAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  44.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  174.75
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl ((S)-6-azido-1-(((S)-1-(((S)-1-hydroxy-3-(4-(prop-2-yn-1-yloxy)phenyl)propan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxohexan-2-yl)carbamate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 7.25h， 以75%的产率得到benzyl N-[(12S,15S,18S)-18-(hydroxymethyl)-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-12-yl]carbamate
  参考文献：
  名称：

  New β-Strand Templates Constrained by Huisgen Cycloaddition

  摘要：

  New peptidic templates constrained into a beta-strand geometry by linking acetylene and azide containing P-1 and P-3 residues of a tripeptide by Huisgen cycloaddition are presented. The conformations of the macrocycles are defined by NMR studies and those that best define a beta-strand are shown to be potent inhibitors of the protease calpain. The beta-strand templates presented and defined here are prepared under optimized conditions that should be suitable for targeting a range of proteases and other applications requiring such a geometry.

  DOI：

  10.1021/ol3002199
• 作为产物：
  描述：

  (S)-2-((叔丁氧基羰基)氨基)-3-(4-(丙-2-炔-1-基氧基)苯基)丙酸甲酯 在 sodium tetrahydroborate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 benzyl ((S)-6-azido-1-(((S)-1-(((S)-1-hydroxy-3-(4-(prop-2-yn-1-yloxy)phenyl)propan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxohexan-2-yl)carbamate
  参考文献：
  名称：

  New β-Strand Templates Constrained by Huisgen Cycloaddition

  摘要：

  New peptidic templates constrained into a beta-strand geometry by linking acetylene and azide containing P-1 and P-3 residues of a tripeptide by Huisgen cycloaddition are presented. The conformations of the macrocycles are defined by NMR studies and those that best define a beta-strand are shown to be potent inhibitors of the protease calpain. The beta-strand templates presented and defined here are prepared under optimized conditions that should be suitable for targeting a range of proteases and other applications requiring such a geometry.

  DOI：

  10.1021/ol3002199