4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)baccatin III | 862378-73-2

• 英文名称: 4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)baccatin III
• CAS: 862378-73-2
• 化学式: C₄₂H₅₀O₁₃
• 分子量: 762.851
• InChiKey: GGBWIMIMFTXYLX-HNTQWEAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  55.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  192.19
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)baccatin III 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)-7-TES-baccatin III
  参考文献：
  名称：

  Syntheses and bioactivities of macrocyclic paclitaxel bis-lactones

  摘要：

  Five macrocyclic paclitaxel bis-lactones and their corresponding open chain taxoids were synthesized as models of the tubulin-binding conformation of paclitaxel. Macrocyclic lactones with a 19-21-membered ring underwent isomerization to form smaller rings. The lactones were evaluated for cytotoxicity and tubulin-polymerization ability. All five macrocyclic paclitaxel lactones were active, but less so than paclitaxel, while the rearranged macrocyclic lactones and the corresponding open-chain taxoids were much less active or inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.002
• 作为产物：
  描述：

  benzyl 6-chloro-6-oxohexanoate 在 吡啶 、 cerium(III) chloride 、 氢氟酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)baccatin III
  参考文献：
  名称：

  Syntheses and bioactivities of macrocyclic paclitaxel bis-lactones

  摘要：

  Five macrocyclic paclitaxel bis-lactones and their corresponding open chain taxoids were synthesized as models of the tubulin-binding conformation of paclitaxel. Macrocyclic lactones with a 19-21-membered ring underwent isomerization to form smaller rings. The lactones were evaluated for cytotoxicity and tubulin-polymerization ability. All five macrocyclic paclitaxel lactones were active, but less so than paclitaxel, while the rearranged macrocyclic lactones and the corresponding open-chain taxoids were much less active or inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.002