(2R,4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-Troc-1,3-oxazolidine | 602319-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-Troc-1,3-oxazolidine
• 英文别名: 5-O-methyl 3-O-(2,2,2-trichloroethyl) (2R,4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
• CAS: 602319-09-5
• 化学式: C₂₁H₂₀Cl₃NO₆
• 分子量: 488.752
• InChiKey: RUSHQHZQGRCRPE-RCCFBDPRSA-N

物化性质

• 沸点：
  565.4±50.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-Troc-1,3-oxazolidine 在 4-二甲氨基吡啶 、 氢氧化钾 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 27.5h， 生成 3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel
  参考文献：
  名称：

  A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct:  Design and Synthesis of Isotaxel

  摘要：

  A novel water-soluble paclitaxel prodrug, isotaxel 2, that realizes a higher water-solubility and the formation of paclitaxel through a simple pH-dependent chemical mechanism via the O-N acyl migration was synthesized and showed promising results in water-solubility and kinetics. This prodrug, a 2'-O-benzoyl isoform of paclitaxel, has no additional functional auxiliaries released during conversion to paclitaxel, which would be a great advantage in toxicology and medical economics.

  DOI：

  10.1021/jm034112n
• 作为产物：
  描述：

  (2R,3S)-3-苯基异丝氨酸盐酸盐 在 sodium hydroxide 、 氯化亚砜 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 15.5h， 生成 (2R,4S,5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-Troc-1,3-oxazolidine
  参考文献：
  名称：

  A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct:  Design and Synthesis of Isotaxel

  摘要：

  A novel water-soluble paclitaxel prodrug, isotaxel 2, that realizes a higher water-solubility and the formation of paclitaxel through a simple pH-dependent chemical mechanism via the O-N acyl migration was synthesized and showed promising results in water-solubility and kinetics. This prodrug, a 2'-O-benzoyl isoform of paclitaxel, has no additional functional auxiliaries released during conversion to paclitaxel, which would be a great advantage in toxicology and medical economics.

  DOI：

  10.1021/jm034112n