tert-butyl [(5R,6R,7S)-6-acetamido-1-oxo-5-(pentan-3-yloxy)-3,4,5,6,7,8-hexahydro-1H-isochromen-7-yl]carbamate | 1448675-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: tert-butyl [(5R,6R,7S)-6-acetamido-1-oxo-5-(pentan-3-yloxy)-3,4,5,6,7,8-hexahydro-1H-isochromen-7-yl]carbamate
• 英文别名: tert-butyl N-[(5R,6R,7S)-6-acetamido-1-oxo-5-pentan-3-yloxy-3,4,5,6,7,8-hexahydroisochromen-7-yl]carbamate
• CAS: 1448675-35-1
• 化学式: C₂₁H₃₄N₂O₆
• 分子量: 410.511
• InChiKey: QAZDISBWGSSRMF-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl [(5R,6R,7S)-6-acetamido-1-oxo-5-(pentan-3-yloxy)-3,4,5,6,7,8-hexahydro-1H-isochromen-7-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以55%的产率得到N-((5R,6R,7S)-7-Amino-1-oxo-5-(pentan-3-yloxy)-3,4,5,6,7,8-hexahydro-1H-isochromen-6-yl)acetamide
  参考文献：
  名称：

  SYNTHESIS OF A NEW OSELTAMIVIR DERIVATIVE THROUGH LATE-STAGE CATALYTIC C–H FUNCTIONALIZATION

  摘要：

  N-Boc-protected oseltamivir 5 was converted to olefin insertion product 4 via a ruthenium-catalyzed C(sp(2))-H functionalization reaction using its ester functionality as a directing group. The addition of a catalytic amount of (p-CF3C6H4)(3)P in the presence of the RuH2(CO)(PPh3)(3) catalyst significantly improved the yield for this specific conversion. Tamao-Fleming oxidation followed by deprotection concisely produced a new oseltamivir analog 16.

  DOI：

  10.3987/com-12-s(n)94
• 作为产物：
  描述：

  奥司他韦 在 N-甲基咪唑 、 potassium hydrogen difluoride 、 RuH₂(CO)(PPh₃)₃ 、 双氧水 、 乙酸酐 、 三(4-三氟甲苯基)膦 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.0h， 生成 tert-butyl [(5R,6R,7S)-6-acetamido-1-oxo-5-(pentan-3-yloxy)-3,4,5,6,7,8-hexahydro-1H-isochromen-7-yl]carbamate
  参考文献：
  名称：

  SYNTHESIS OF A NEW OSELTAMIVIR DERIVATIVE THROUGH LATE-STAGE CATALYTIC C–H FUNCTIONALIZATION

  摘要：

  N-Boc-protected oseltamivir 5 was converted to olefin insertion product 4 via a ruthenium-catalyzed C(sp(2))-H functionalization reaction using its ester functionality as a directing group. The addition of a catalytic amount of (p-CF3C6H4)(3)P in the presence of the RuH2(CO)(PPh3)(3) catalyst significantly improved the yield for this specific conversion. Tamao-Fleming oxidation followed by deprotection concisely produced a new oseltamivir analog 16.

  DOI：

  10.3987/com-12-s(n)94

文献信息

• SYNTHESIS OF A NEW OSELTAMIVIR DERIVATIVE THROUGH LATE-STAGE CATALYTIC C–H FUNCTIONALIZATION
  作者：Motomu Kanai、Kenta Saito

  DOI：10.3987/com-12-s(n)94

  日期：——

  N-Boc-protected oseltamivir 5 was converted to olefin insertion product 4 via a ruthenium-catalyzed C(sp(2))-H functionalization reaction using its ester functionality as a directing group. The addition of a catalytic amount of (p-CF3C6H4)(3)P in the presence of the RuH2(CO)(PPh3)(3) catalyst significantly improved the yield for this specific conversion. Tamao-Fleming oxidation followed by deprotection concisely produced a new oseltamivir analog 16.