9-deacetyl-1-deoxybaccatin VI | 1310814-89-1

• 英文名称: 9-deacetyl-1-deoxybaccatin VI
• CAS: 1310814-89-1
• 化学式: C₃₅H₄₄O₁₂
• 分子量: 656.727
• InChiKey: YDFWHTKAVWFXOL-OTQZIHIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  47.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  160.96
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  9-deacetyl-1-deoxybaccatin VI 在 盐酸 、 4-二甲氨基吡啶 、 四丙基高钌酸铵 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 7-ethanoyl-10-n-hexanoyl-10-deacetyl-1-deoxypaclitaxel
  参考文献：
  名称：

  Semi-synthesis of 1-Deoxypaclitaxel and its Analogues from 1-Deoxybaccatin VI

  摘要：

  Despite numerous synthetic efforts and extensive SAR studies on paclitaxel analogs, little work has been devoted to derive SAR of the C-1 hydroxy group. Up to now, 1-deoxypaclitaxel has only been reported to be isolated from the Chinese yew, Taxus mairei (Taxaceae). However, the isolation from natural sources does not solve the availability problem due to the reported low yield of isolation. Also, only several analogues of this type have been reported. Thus, there is an urgent need for exploration of new synthetic methods on this structurally intriguing molecule and further SAR studies. In present work, we report the initial expedient semi-synthesis of 1-deoxypaclitaxel and its novel analogues with structural variations at C7 and C10 from 1-deoxybaccatin VI, as well as their cytotoxic activities against A 549 cell line.

  DOI：

  10.2174/157340612802084379
• 作为产物：
  描述：

  7,9,10-trideacetyl-1-deoxybaccatin VI 在 4-二甲氨基吡啶 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 9-deacetyl-1-deoxybaccatin VI
  参考文献：
  名称：

  Semi-synthesis of 1-Deoxypaclitaxel and its Analogues from 1-Deoxybaccatin VI

  摘要：

  Despite numerous synthetic efforts and extensive SAR studies on paclitaxel analogs, little work has been devoted to derive SAR of the C-1 hydroxy group. Up to now, 1-deoxypaclitaxel has only been reported to be isolated from the Chinese yew, Taxus mairei (Taxaceae). However, the isolation from natural sources does not solve the availability problem due to the reported low yield of isolation. Also, only several analogues of this type have been reported. Thus, there is an urgent need for exploration of new synthetic methods on this structurally intriguing molecule and further SAR studies. In present work, we report the initial expedient semi-synthesis of 1-deoxypaclitaxel and its novel analogues with structural variations at C7 and C10 from 1-deoxybaccatin VI, as well as their cytotoxic activities against A 549 cell line.

  DOI：

  10.2174/157340612802084379