methyl (2S)-2-[[ethenyl-[ethenyl-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]-prop-2-enylamino]phosphoryl]oxyphosphoryl]-prop-2-enylamino]-4-methylpentanoate | 288620-44-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[[ethenyl-[ethenyl-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]-prop-2-enylamino]phosphoryl]oxyphosphoryl]-prop-2-enylamino]-4-methylpentanoate
• CAS: 288620-44-0
• 化学式: C₂₄H₄₂N₂O₇P₂
• 分子量: 532.554
• InChiKey: MACUASCIOCXFKX-AEFSKKNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[ethenyl-[ethenyl-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]-prop-2-enylamino]phosphoryl]oxyphosphoryl]-prop-2-enylamino]-4-methylpentanoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到methyl (2S)-2-[(2R)-2-[[(2S)-1-[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]-2-oxo-5H-1,2λ5-azaphosphol-2-yl]oxy]-2-oxo-5H-1,2λ5-azaphosphol-1-yl]-4-methylpentanoate
  参考文献：
  名称：

  The Synthesis of P-Chiral Amino Acid-Derived Phosphonamidic Anhydrides

  摘要：

  The synthesis of an array of P-chiral amino acid-derived phosphonamidic anhydrides is described. These anhydrides are prepared by condensation of allylated amino acids 19-22 with methyl- or vinylphosphonic dichlorides 23 or 24 to produce three diastereomeric anhydrides 4-11a-c in good to excellent yields. The mechanistic issues concerning anhydride formation are discussed and supported by experimental results. Vinylphosphonamidic anhydrides 8-11 are further derivatized via the ring-closing metathesis (RCM) reaction to yield amino acid-derived bicyclic phosphonamidic anhydrides.

  DOI：

  10.1021/jo000631b
• 作为产物：
  描述：

  N-allyl (L)-leucine methyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S)-2-[[ethenyl-[ethenyl-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]-prop-2-enylamino]phosphoryl]oxyphosphoryl]-prop-2-enylamino]-4-methylpentanoate
  参考文献：
  名称：

  The Synthesis of P-Chiral Amino Acid-Derived Phosphonamidic Anhydrides

  摘要：

  The synthesis of an array of P-chiral amino acid-derived phosphonamidic anhydrides is described. These anhydrides are prepared by condensation of allylated amino acids 19-22 with methyl- or vinylphosphonic dichlorides 23 or 24 to produce three diastereomeric anhydrides 4-11a-c in good to excellent yields. The mechanistic issues concerning anhydride formation are discussed and supported by experimental results. Vinylphosphonamidic anhydrides 8-11 are further derivatized via the ring-closing metathesis (RCM) reaction to yield amino acid-derived bicyclic phosphonamidic anhydrides.

  DOI：

  10.1021/jo000631b

文献信息

• The Synthesis of <i>P</i>-Chiral Amino Acid-Derived Phosphonamidic Anhydrides
  作者：Kevin T. Sprott、Paul R. Hanson

  DOI：10.1021/jo000631b

  日期：2000.7.1

  The synthesis of an array of P-chiral amino acid-derived phosphonamidic anhydrides is described. These anhydrides are prepared by condensation of allylated amino acids 19-22 with methyl- or vinylphosphonic dichlorides 23 or 24 to produce three diastereomeric anhydrides 4-11a-c in good to excellent yields. The mechanistic issues concerning anhydride formation are discussed and supported by experimental results. Vinylphosphonamidic anhydrides 8-11 are further derivatized via the ring-closing metathesis (RCM) reaction to yield amino acid-derived bicyclic phosphonamidic anhydrides.