methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]amino]propanoate | 1053633-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]amino]propanoate
• CAS: 1053633-87-6
• 化学式: C₄₅H₅₁N₈O₁₄P
• 分子量: 958.919
• InChiKey: OUQDIKOCISIPSK-RLIJUHMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  233
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]amino]propanoate 在 甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]amino]propanoate
  参考文献：
  名称：

  Synthesis and Resolution of Dinucleotide(TpAZT) Phosphoramidates

  摘要：

  Dinucleotide (TpAZT) phosphoramidates were synthesized through Atherton-Todd reaction of dinucleoside H-phosphonates and amino acid methyl esters, and their diastereomers (R-p and S-p) were separated by crystallization. It was showed that the cheap methyl esters of natural alanine and phenylalanine could act as new chiral auxiliaries for large-scale synthesis of dinucleotide analogs.

  DOI：

  10.1081/scc-120021847
• 作为产物：
  描述：

  Phenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 在 水 、 三甲基乙酰氯 、 三乙胺 作用下， 以 吡啶 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]amino]propanoate
  参考文献：
  名称：

  Synthesis and Resolution of Dinucleotide(TpAZT) Phosphoramidates

  摘要：

  Dinucleotide (TpAZT) phosphoramidates were synthesized through Atherton-Todd reaction of dinucleoside H-phosphonates and amino acid methyl esters, and their diastereomers (R-p and S-p) were separated by crystallization. It was showed that the cheap methyl esters of natural alanine and phenylalanine could act as new chiral auxiliaries for large-scale synthesis of dinucleotide analogs.

  DOI：

  10.1081/scc-120021847

文献信息

• Synthesis and Resolution of Dinucleotide(TpAZT) Phosphoramidates
  作者：Changxue Lin、Hua Fu、Guangzhong Tu、Yufen Zhao

  DOI：10.1081/scc-120021847

  日期：2003.1.8

  Dinucleotide (TpAZT) phosphoramidates were synthesized through Atherton-Todd reaction of dinucleoside H-phosphonates and amino acid methyl esters, and their diastereomers (R-p and S-p) were separated by crystallization. It was showed that the cheap methyl esters of natural alanine and phenylalanine could act as new chiral auxiliaries for large-scale synthesis of dinucleotide analogs.