4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)-7-TES-baccatin III | 817207-71-9

• 英文名称: 4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)-7-TES-baccatin III
• CAS: 817207-71-9
• 化学式: C₄₈H₆₄O₁₃Si
• 分子量: 877.114
• InChiKey: VXDAZZIXZOWZCX-LCELOUBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  62.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  181.19
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-benzoyl-4-(3-(benzyloxy)phenyl)-3-TIPS-azetidin-2-one 、 4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)-7-TES-baccatin III 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 4-deacetyl-4-(5-benzyloxycarbonylpentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel
  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 、 咪唑 、 cerium(III) chloride 、 氢氟酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 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