4(S)-(benzyloxy)-3(R)-(chloromethoxy)-1-(diethylphosphonyl)pentane | 174359-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4(S)-(benzyloxy)-3(R)-(chloromethoxy)-1-(diethylphosphonyl)pentane
• CAS: 174359-09-2
• 化学式: C₁₇H₂₈ClO₅P
• 分子量: 378.833
• InChiKey: BIYWUBNXXWSCGK-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  24.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4(S)-(benzyloxy)-3(R)-(chloromethoxy)-1-(diethylphosphonyl)pentane 在 palladium dihydroxide 、 sodium hydroxide 、 乙醇 、 四丁基碘化铵 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-<<1-(ethylphosphonyl)-4(S)-hydroxy-3(R)-pentoxy>methyl>uracil
  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：

  聚合甲醛 、 Diethyl (3R,4S)-4-(benzyloxy)-3-hydroxypentanephosphonate 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4(S)-(benzyloxy)-3(R)-(chloromethoxy)-1-(diethylphosphonyl)pentane
  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