Benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-carboxy-2-phenyl-ethyl ester | 188402-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: Benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-carboxy-2-phenyl-ethyl ester
• 英文别名: (2R,3S)-2-benzoyloxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid
• CAS: 188402-08-6
• 化学式: C₂₁H₂₃NO₆
• 分子量: 385.417
• InChiKey: GUFUCRZWZBVRML-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-carboxy-2-phenyl-ethyl ester 在 盐酸 、 4-二甲氨基吡啶 、 苯甲醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (1R,2S)-2-amino-1-[(cyclohexyloxy)carbonyl]-2-phenylethyl benzoate hydrochloride
  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：

  苯甲酰氯 、 (2R,3S)-3-叔丁氧甲酰胺基-2-羟基-3-苯基-丙胺酸 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-carboxy-2-phenyl-ethyl ester
  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

文献信息

• A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct:  Design and Synthesis of Isotaxel
  作者：Yoshio Hayashi、Mariusz Skwarczynski、Yoshio Hamada、Youhei Sohma、Tooru Kimura、Yoshiaki Kiso

  DOI：10.1021/jm034112n

  日期：2003.8.1

  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.