(2S,4R)-5-benzoyloxy-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid | 753487-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R)-5-benzoyloxy-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 753487-52-4
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: XZVMUIQDICUJTC-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  聚合甲醛 、 (2S,4R)-5-benzoyloxy-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 32.0h， 以3.76 g的产率得到tert-butyl (4S)-4-[(2R)-3-benzoyloxy-2-methylpropyl]-5-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n
• 作为产物：
  描述：

  Benzoic acid (2R,4S)-5-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-4-tert-butoxycarbonylamino-2-methyl-5-oxo-pentyl ester 在 双氧水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.17h， 生成 (2S,4R)-5-benzoyloxy-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n

文献信息

• Total Synthesis of Cyclomarin C
  作者：Shi-Jun Wen、Zhu-Jun Yao

  DOI：10.1021/ol049065n

  日期：2004.8.1

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.