1-[(2R,4S,5S)-4-azido-5-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 637014-44-9

• 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: 1-[(2R,4S,5S)-4-azido-5-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 637014-44-9
• 化学式: C₄₁H₄₄N₇O₁₂P
• 分子量: 857.814
• InChiKey: OTJLAJSOCOJRQA-UWNKZCSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  195
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5S)-4-azido-5-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 甲酸 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 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]-3-methylbutanoate
  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 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 1-[(2R,4S,5S)-4-azido-5-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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 of AZT/d4T Boranophosphates as Anti-HIV Prodrug Candidates
  作者：Hua Fu、Yufen Zhao、Changxue Lin、Guangzhong Tu

  DOI：10.1055/s-2004-815939

  日期：——

  AZT/d4T phosphonates were synthesized by sequential condensation of AZT/d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.

  AZT/d4T膦酸盐是通过在异戊酰氯存在下，依次将AZT/d4T与相应的醇或5′-DMT胸苷缩合合成的。这些膦酸盐依次进行硅烷化、硼化及在氨水中水解，得到抗HIV前药候选物AZT/d4T硼膦酸盐。
• 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.