[(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-benzoyloxy-2-[[[[(3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoyl]amino]-phenylmethoxyphosphoryl]oxymethyl]oxolan-3-yl] benzoate | 442675-43-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-benzoyloxy-2-[[[[(3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoyl]amino]-phenylmethoxyphosphoryl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 442675-43-6
• 化学式: C₅₇H₅₀N₇O₁₄P
• 分子量: 1088.04
• InChiKey: YNEMXVZUODCGMY-XPCCDXLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  79
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  264
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-benzoyloxy-2-[[[[(3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoyl]amino]-phenylmethoxyphosphoryl]oxymethyl]oxolan-3-yl] benzoate 在 palladium on activated charcoal 1,4-环己二烯 、 ammonium hydroxide 作用下， 以 甲醇 、 乙醇 、 1,4-二氧六环 为溶剂， 反应 13.0h， 生成 (S)-2-Amino-4-{[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphorylamino}-4-oxo-butyric acid; compound with ammonia
  参考文献：
  名称：

  A Concise Synthesis of β-Asparaginyladenylate

  摘要：

  Stable analogues of acyladenylate intermediates, such as N-acylphosphoramidates, are useful probes of tRNA aminoacylation and enzyme mechanism, and have potential application as enzyme inhibitors. We now report a concise, "one-pot" synthesis of beta-asparaginyladenylate using a novel coupling protocol that yields the target N-acylphosphoramidate in three reactions from readily available precursors. This simple synthetic procedure may represent a general approach for the preparation of functionalized N-acylphosphoramidates from amides that do not undergo coupling under the conditions of existing literature protocols.

  DOI：

  10.1021/jo025510l
• 作为产物：
  描述：

  [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-benzoyloxy-2-[[[[(3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoyl]amino]-phenylmethoxyphosphanyl]oxymethyl]oxolan-3-yl] benzoate 在 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以88%的产率得到[(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-benzoyloxy-2-[[[[(3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoyl]amino]-phenylmethoxyphosphoryl]oxymethyl]oxolan-3-yl] benzoate
  参考文献：
  名称：

  A Concise Synthesis of β-Asparaginyladenylate

  摘要：

  Stable analogues of acyladenylate intermediates, such as N-acylphosphoramidates, are useful probes of tRNA aminoacylation and enzyme mechanism, and have potential application as enzyme inhibitors. We now report a concise, "one-pot" synthesis of beta-asparaginyladenylate using a novel coupling protocol that yields the target N-acylphosphoramidate in three reactions from readily available precursors. This simple synthetic procedure may represent a general approach for the preparation of functionalized N-acylphosphoramidates from amides that do not undergo coupling under the conditions of existing literature protocols.

  DOI：

  10.1021/jo025510l