methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17R)-17-ethynyl-13-methoxycarbonyl-17-trimethylsilyloxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate | 959633-85-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17R)-17-ethynyl-13-methoxycarbonyl-17-trimethylsilyloxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
• CAS: 959633-85-3
• 化学式: C₄₉H₆₂N₄O₉Si
• 分子量: 879.138
• InChiKey: BGWZAGFSSMGEBZ-VWDDQESPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  63
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17R)-17-ethynyl-13-methoxycarbonyl-17-trimethylsilyloxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以99%的产率得到methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17R)-17-ethynyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
  参考文献：
  名称：

  Synthesis of (+)-Vinblastine and Its Analogues

  摘要：

  A synthetic route to vinblastine and its analogues with an ethynyl group, which features a stereoselective coupling of an 11-membered key intermediate with vindoline, is described. Transformations of the alkynyl moiety including a partial reduction as well as a Sonogashira coupling furnished a variety of analogues.

  DOI：

  10.1021/ol702040y
• 作为产物：
  描述：

  C₅₆H₇₀N₄O₁₂SSi 在 碳酸氢钠 作用下， 以 水 、 异丙醇 、 乙腈 为溶剂， 反应 3.0h， 以91%的产率得到methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17R)-17-ethynyl-13-methoxycarbonyl-17-trimethylsilyloxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
  参考文献：
  名称：

  Synthesis of (+)-Vinblastine and Its Analogues

  摘要：

  A synthetic route to vinblastine and its analogues with an ethynyl group, which features a stereoselective coupling of an 11-membered key intermediate with vindoline, is described. Transformations of the alkynyl moiety including a partial reduction as well as a Sonogashira coupling furnished a variety of analogues.

  DOI：

  10.1021/ol702040y