(4S,3R)-4-(4-azidophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one | 819849-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4S,3R)-4-(4-azidophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (3R,4S)-4-(4-azidophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 819849-36-0
• 化学式: C₁₆H₁₄N₄O₃
• 分子量: 310.312
• InChiKey: QFANBCWIBNEPSI-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,3R)-4-(4-azidophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one 在 咪唑 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 TEA 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (4S,3R)-4-[4-(azidophenyl)]-3-tert-butyldimethylsiloxy-1-(phenylcarbonyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis and Anti-Tubulin Activity of a 3‘-(4-Azidophenyl)-3‘-dephenylpaclitaxel Photoaffinity Probe

  摘要：

  The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3'-(4-azidophenyl)-3'-dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.

  DOI：

  10.1021/jm030581d
• 作为产物：
  描述：

  对氨基苯甲醇 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium dihydrogenphosphate 、 草酰氯 、 Pseudomonas cepacia lipase 、 TEA 、 硫酸 、 N,N-二甲基甲酰胺 、 pyridinium chlorochromate 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 29.75h， 生成 (4S,3R)-4-(4-azidophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis and Anti-Tubulin Activity of a 3‘-(4-Azidophenyl)-3‘-dephenylpaclitaxel Photoaffinity Probe

  摘要：

  The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3'-(4-azidophenyl)-3'-dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.

  DOI：

  10.1021/jm030581d

文献信息

• Synthesis and Anti-Tubulin Activity of a 3‘-(4-Azidophenyl)-3‘-dephenylpaclitaxel Photoaffinity Probe
  作者：Jared T. Spletstoser、Patrick T. Flaherty、Richard H. Himes、Gunda I. Georg

  DOI：10.1021/jm030581d

  日期：2004.12.1

  The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3'-(4-azidophenyl)-3'-dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.