2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-4-deacetyl-4-(O-benzylglutaryl)-paclitaxel | 330996-43-5

• 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: 2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-4-deacetyl-4-(O-benzylglutaryl)-paclitaxel
• CAS: 330996-43-5
• 化学式: C₆₉H₈₉NO₁₆Si₂
• 分子量: 1244.63
• InChiKey: SMKUOUSVVIJMAS-UBOHQGBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.69
• 重原子数：
  88.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  225.59
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-4-deacetyl-4-(O-benzylglutaryl)-paclitaxel 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以71%的产率得到4-deacetyl-4-(O-benzylglutaryl)-paclitaxel
  参考文献：
  名称：

  Synthesis and bioactivity of 2,4-diacyl analogues of paclitaxel

  摘要：

  The 2,4-diacyl paclitaxel analogues 8a-8r were prepared from paclitaxel by acylation of 4-deacetyl-2-debenzoylpaclitaxel 1,2-carbonate (3) followed either by hydrolysis of the carbonate and acylation or by direct treatment of the carbonate with an aryllithium. Some of the resulting derivatives showed significantly improved tubulin assembly activity and cytotoxicity as compared with paclitaxel; in some cases this improvement was especially significant for paclitaxel-resistant cell lines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00233-9
• 作为产物：
  描述：

  2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-2-debenzoyl-4-deacetyl-1,2-carbonato-paclitaxel 在 4-二甲氨基吡啶 、 lithium hydroxide 、 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 74.0h， 生成 2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-4-deacetyl-4-(O-benzylglutaryl)-paclitaxel
  参考文献：
  名称：

  Synthesis and bioactivity of 2,4-diacyl analogues of paclitaxel

  摘要：

  The 2,4-diacyl paclitaxel analogues 8a-8r were prepared from paclitaxel by acylation of 4-deacetyl-2-debenzoylpaclitaxel 1,2-carbonate (3) followed either by hydrolysis of the carbonate and acylation or by direct treatment of the carbonate with an aryllithium. Some of the resulting derivatives showed significantly improved tubulin assembly activity and cytotoxicity as compared with paclitaxel; in some cases this improvement was especially significant for paclitaxel-resistant cell lines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00233-9