2-amino-6-(benzyloxy)-9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>purine | 174358-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-amino-6-(benzyloxy)-9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>purine
• 英文别名: 9-[[(3R,4S)-1-diethoxyphosphoryl-4-phenylmethoxypentan-3-yl]oxymethyl]-6-phenylmethoxypurin-2-amine
• CAS: 174358-90-8
• 化学式: C₂₉H₃₈N₅O₆P
• 分子量: 583.624
• InChiKey: AUUWPRQIAFJSPP-WIOPSUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-amino-6-(benzyloxy)-9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>purine 在 palladium dihydroxide 、 乙醇 、 环己烯 作用下， 反应 1.5h， 以60%的产率得到9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>guanine
  参考文献：
  名称：

  Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides

  摘要：

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.

  DOI：

  10.1021/jo951701v
• 作为产物：
  描述：

  Diethyl (3R,4S)-4-(benzyloxy)-3-hydroxypentanephosphonate 在 盐酸 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-amino-6-(benzyloxy)-9-<<4(S)-(benzyloxy)-1-(diethylphosphonyl)-3(R)-pentoxy>methyl>purine
  参考文献：
  名称：

  Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides

  摘要：

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.

  DOI：

  10.1021/jo951701v