3-O-tert-butyl 4-O-methyl (1S,4R,6S,7Z,14S,18S)-14-(cyclopentyloxycarbonylamino)-18-[(4-nitrophenyl)methoxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-3,4-dicarboxylate | 1108600-91-4

• 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: 3-O-tert-butyl 4-O-methyl (1S,4R,6S,7Z,14S,18S)-14-(cyclopentyloxycarbonylamino)-18-[(4-nitrophenyl)methoxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-3,4-dicarboxylate
• CAS: 1108600-91-4
• 化学式: C₃₇H₅₀N₄O₁₁
• 分子量: 726.824
• InChiKey: AIYQMRARKKWFEC-ZJIDPQPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  52
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  187
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-O-tert-butyl 4-O-methyl (1S,4R,6S,7Z,14S,18S)-14-(cyclopentyloxycarbonylamino)-18-[(4-nitrophenyl)methoxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-3,4-dicarboxylate 在 苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以95%的产率得到(Z)-(1S,4R,6S,14S,18S)-14-Cyclopentyloxycarbonylamino-18-(4-nitro-benzyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-7-ene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Second-Generation Process for the HCV Protease Inhibitor BILN 2061: A Greener Approach to Ru-Catalyzed Ring-Closing Metathesis

  摘要：

  The ring-closing metathesis (RCM) step, a key reaction in our process to BILN 2061, was dramatically improved from the first-generation process by the selection of a more appropriate substrate as well as the use of a more effective catalyst. The two RCM reactions are compared in detail using criteria that are of high significance to the process chemist.

  DOI：

  10.1021/op800225f
• 作为产物：
  描述：

  在 1,3-bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)dichloro(5-nitro-2-isopropoxyphenylmethylene)ruthenium 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以95%的产率得到3-O-tert-butyl 4-O-methyl (1S,4R,6S,7Z,14S,18S)-14-(cyclopentyloxycarbonylamino)-18-[(4-nitrophenyl)methoxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-3,4-dicarboxylate
  参考文献：
  名称：

  Second-Generation Process for the HCV Protease Inhibitor BILN 2061: A Greener Approach to Ru-Catalyzed Ring-Closing Metathesis

  摘要：

  The ring-closing metathesis (RCM) step, a key reaction in our process to BILN 2061, was dramatically improved from the first-generation process by the selection of a more appropriate substrate as well as the use of a more effective catalyst. The two RCM reactions are compared in detail using criteria that are of high significance to the process chemist.

  DOI：

  10.1021/op800225f