7,13-Bis(triethylsilyl)baccatin 1-xanthane | 155370-93-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7,13-Bis(triethylsilyl)baccatin 1-xanthane
• CAS: 155370-93-7
• 化学式: C₄₅H₆₈O₁₁S₂Si₂
• 分子量: 905.331
• InChiKey: JGLSVPINPQTELD-IOEIIUTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.38
• 重原子数：
  60.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  7,13-Bis(triethylsilyl)baccatin 1-xanthane 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  The Chemistry of Taxanes: Skeletal Rearrangements of Baccatin Derivatives via Radical Intermediates

  摘要：

  In the course of a synthetic program aimed at systematic defunctionalization of the taxol core for structure activity studies, a number of radical-based deoxygenation reactions were carried out on baccatin III derivatives. In this connection, we have discovered that formation of radicals at positions C-1, C-2, and C-7 in the taxane core of baccatin III results in a number of skeletal rearrangement cascades. Furthermore, the exact composition of the product mixture depends on the specific tin (or silicon) hydride used for the reduction. In the case of C-2- and C-7-derived radicals, direct quenching with tin hydrides without rearrangement was possible under some conditions. However, we were unable to find conditions to quench the C-1 radical, since rearrangement pathways always predominate in this case.

  DOI：

  10.1021/jo00085a040
• 作为产物：
  描述：

  巴卡丁 III 在 咪唑 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 7,13-Bis(triethylsilyl)baccatin 1-xanthane
  参考文献：
  名称：

  The Chemistry of Taxanes: Skeletal Rearrangements of Baccatin Derivatives via Radical Intermediates

  摘要：

  In the course of a synthetic program aimed at systematic defunctionalization of the taxol core for structure activity studies, a number of radical-based deoxygenation reactions were carried out on baccatin III derivatives. In this connection, we have discovered that formation of radicals at positions C-1, C-2, and C-7 in the taxane core of baccatin III results in a number of skeletal rearrangement cascades. Furthermore, the exact composition of the product mixture depends on the specific tin (or silicon) hydride used for the reduction. In the case of C-2- and C-7-derived radicals, direct quenching with tin hydrides without rearrangement was possible under some conditions. However, we were unable to find conditions to quench the C-1 radical, since rearrangement pathways always predominate in this case.

  DOI：

  10.1021/jo00085a040