methyl (1R,21S,24S)-21-tert-butyl-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.14,7.06,11]heptacosa-6(11),7,9,13-tetraene-24-carboxylate | 1372882-61-5

• 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 (1R,21S,24S)-21-tert-butyl-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.14,7.06,11]heptacosa-6(11),7,9,13-tetraene-24-carboxylate
• CAS: 1372882-61-5
• 化学式: C₃₀H₄₁N₃O₇
• 分子量: 555.671
• InChiKey: SNPSRYWOOMCJPH-YFNKSVMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (1R,21S,24S)-21-tert-butyl-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.14,7.06,11]heptacosa-6(11),7,9,13-tetraene-24-carboxylate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 生成 methyl (1R,21S,24S)-21-tert-butyl-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.1(4,7).0(6,11)]heptacosa-6,8,10-triene-24-carboxylate
  参考文献：
  名称：

  Synthesis of the HCV Protease Inhibitor Vaniprevir (MK-7009) Using Ring-Closing Metathesis Strategy

  摘要：

  A highly efficient synthesis of Vaniprevir (MK-7009) has been accomplished in nine linear steps and 55% overall yield. The key features of this synthesis include a cost-effective synthesis of the isoindoline subunit and efficient construction of the 20-membered macrocyclic core of Vaniprevir (MK-7009) utilizing ring-closing metathesis technology. A high-performing ring-closing metathesis protocol has been achieved by simultaneous slow addition of the ruthenium catalyst (0.2 mol %) and the diene substrate at a concentration of 0.13 M.

  DOI：

  10.1021/jo3001595
• 作为产物：
  描述：

  2,2-dimethylpent-4-en-1-ol 在 吡啶 、 Hoveyda-Grubbs catalyst second generation 、 2,6-二氯-1,4-苯醌 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 methyl (1R,21S,24S)-21-tert-butyl-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.14,7.06,11]heptacosa-6(11),7,9,13-tetraene-24-carboxylate
  参考文献：
  名称：

  Synthesis of the HCV Protease Inhibitor Vaniprevir (MK-7009) Using Ring-Closing Metathesis Strategy

  摘要：

  A highly efficient synthesis of Vaniprevir (MK-7009) has been accomplished in nine linear steps and 55% overall yield. The key features of this synthesis include a cost-effective synthesis of the isoindoline subunit and efficient construction of the 20-membered macrocyclic core of Vaniprevir (MK-7009) utilizing ring-closing metathesis technology. A high-performing ring-closing metathesis protocol has been achieved by simultaneous slow addition of the ruthenium catalyst (0.2 mol %) and the diene substrate at a concentration of 0.13 M.

  DOI：

  10.1021/jo3001595

文献信息

• Synthesis of the HCV Protease Inhibitor Vaniprevir (MK-7009) Using Ring-Closing Metathesis Strategy
  作者：Jongrock Kong、Cheng-yi Chen、Jaume Balsells-Padros、Yang Cao、Robert F. Dunn、Sarah J. Dolman、Jacob Janey、Hongmei Li、Michael J. Zacuto

  DOI：10.1021/jo3001595

  日期：2012.4.20

  A highly efficient synthesis of Vaniprevir (MK-7009) has been accomplished in nine linear steps and 55% overall yield. The key features of this synthesis include a cost-effective synthesis of the isoindoline subunit and efficient construction of the 20-membered macrocyclic core of Vaniprevir (MK-7009) utilizing ring-closing metathesis technology. A high-performing ring-closing metathesis protocol has been achieved by simultaneous slow addition of the ruthenium catalyst (0.2 mol %) and the diene substrate at a concentration of 0.13 M.