2'-O-acetyl-5'-O-benzoyl-3'-deoxy-3'-ethoxycarbonylmethyl-uridine | 1173826-15-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-3'-ethoxycarbonylmethyl-uridine
• CAS: 1173826-15-7
• 化学式: C₂₂H₂₄N₂O₉
• 分子量: 460.441
• InChiKey: JBOXXKUEYYLFHR-XNFNUYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  142.99
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethyl-D-ribofuranose 、 尿嘧啶 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 水 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以73%的产率得到2'-O-acetyl-5'-O-benzoyl-3'-deoxy-3'-ethoxycarbonylmethyl-uridine
  参考文献：
  名称：

  Synthesis of 3′-deoxy-3′-carboxymethylnucleosides, precursors of oligonucleotides with an amide internucleoside bond

  摘要：

  An improved method for the synthesis of 3-deoxy-3-carboxymethyl nucleosides was suggested. Oxidation of 5-O-benzoyl-1,2-O-isopropylidene-alpha-D-xylofuranose resulted in the 3-keto derivative, which was treated with triethylphosphonoacetate in the presence of sodium hydride to obtain the 3-deoxy-3-ethoxycarbonylmethylene derivative. Hydrogenation of the unsaturated compound proceeded strictly stereospecifically and gave the product with the ribo-configuration. Acetolysis of the resulting compound with AcOH-Ac2O-CH3SO3H led to 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethyl-D-ribofuranose, whose interaction with persilylated nucleic bases gave 3-deoxy-3-ethoxycarbonylmethylnucleosides in a total yield of 42-49% from the starting compound.

  DOI：

  10.1134/s1068162009010099