(3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-azetidin-2-one | 178207-68-6

• 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: (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-azetidin-2-one
• 英文别名: (3R,4S)-1-benzoyl-3-[tert-butyl(dimethyl)silyl]oxy-4-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]azetidin-2-one
• CAS: 178207-68-6
• 化学式: C₂₈H₄₁NO₄Si₂
• 分子量: 511.809
• InChiKey: DPLIVCAYSHLNOW-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-azetidin-2-one 在 吡啶 、 sodium hydride 、 氟化氢吡啶 作用下， 反应 12.5h， 生成 3'-P-羟基紫杉醇
  参考文献：
  名称：

  Preparation of Phenolic Paclitaxel Metabolites

  摘要：

  The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.

  DOI：

  10.1021/jm960142x
• 作为产物：
  描述：

  4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 14.83h， 生成 (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-azetidin-2-one
  参考文献：
  名称：

  Preparation of Phenolic Paclitaxel Metabolites

  摘要：

  The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.

  DOI：

  10.1021/jm960142x

文献信息

• Preparation of Phenolic Paclitaxel Metabolites
  作者：Haeil Park、Michael Hepperle、Thomas C. Boge、Richard H. Himes、Gunda I. Georg

  DOI：10.1021/jm960142x

  日期：1996.1.1

  The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.