tert-butyl (5S,6S,E)-5-(((S)-2-((3-(4-((R)-1-((tert-butoxycarbonyl)amino)-2-(3-chloro-4-methoxyphenyl)ethyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethylpropanoyl)oxy)-4-methylpentanoyl)oxy)-6-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)hept-2-enoate | 1209778-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (5S,6S,E)-5-(((S)-2-((3-(4-((R)-1-((tert-butoxycarbonyl)amino)-2-(3-chloro-4-methoxyphenyl)ethyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethylpropanoyl)oxy)-4-methylpentanoyl)oxy)-6-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)hept-2-enoate
• CAS: 1209778-25-5
• 化学式: C₄₉H₆₉ClN₄O₁₁
• 分子量: 925.56
• InChiKey: ZJOPOOIQNUSFNY-WFFNTWAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.46
• 重原子数：
  65.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  175.63
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (5S,6S,E)-5-(((S)-2-((3-(4-((R)-1-((tert-butoxycarbonyl)amino)-2-(3-chloro-4-methoxyphenyl)ethyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethylpropanoyl)oxy)-4-methylpentanoyl)oxy)-6-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)hept-2-enoate 在 水 、 三氟乙酸 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 以74%的产率得到
  参考文献：
  名称：

  “Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue

  摘要：

  An endocyclic trans-amide linkage within the macrocyclic antitumor agent cryptophycin-52 was replaced by a 1,4-disubstituted 1H-1,2,3-triazole ring. Macrocyclisation of the triazole analogue was accomplished by macrolactamization as well as by Cu(I)-mediated "click"-cyclization. Compared to cryptophycin-52, in vitro cytotoxicity of "clicktophycin-52" against the multidrug resistant human cancer cell line KB-V1 is only slightly reduced.

  DOI：

  10.1021/ol1000473
• 作为产物：
  描述：

  (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate 、 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到tert-butyl (5S,6S,E)-5-(((S)-2-((3-(4-((R)-1-((tert-butoxycarbonyl)amino)-2-(3-chloro-4-methoxyphenyl)ethyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethylpropanoyl)oxy)-4-methylpentanoyl)oxy)-6-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)hept-2-enoate
  参考文献：
  名称：

  “Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue

  摘要：

  An endocyclic trans-amide linkage within the macrocyclic antitumor agent cryptophycin-52 was replaced by a 1,4-disubstituted 1H-1,2,3-triazole ring. Macrocyclisation of the triazole analogue was accomplished by macrolactamization as well as by Cu(I)-mediated "click"-cyclization. Compared to cryptophycin-52, in vitro cytotoxicity of "clicktophycin-52" against the multidrug resistant human cancer cell line KB-V1 is only slightly reduced.

  DOI：

  10.1021/ol1000473