2',3',5'-tri-O-benzoyl-5-methylcytidine | 59237-68-2

• 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',3',5'-tri-O-benzoyl-5-methylcytidine
• CAS: 59237-68-2
• 化学式: C₃₁H₂₇N₃O₈
• 分子量: 569.571
• InChiKey: ZIMDOHREDVDBGV-DLGLWYJGSA-N

物化性质

• 沸点：
  722.0±70.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  149.04
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-benzoyl-5-methylcytidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以91%的产率得到5-甲基胞苷
  参考文献：
  名称：

  Recognition of RNA by triplex formation: Divergent effects of pyrimidine C-5 methylation

  摘要：

  In DNA triple helices, methylation at C-5 of thymine or cytosine is reported to have similar stabilizing effects for both bases. Here we show, however, that methylation of the same positions in RNA triplexes has distinctly different effects than in DNA. We have previously described the use of circular tripler-forming RNA oligonucleotides to recognize RNA sequences. Here it is shown that addition of C-5 methyl groups to uracils in these compounds very significantly increases not only affinity but also sequence selectivity in binding a purine-rich RNA target, as measured by thermal denaturation with various target RNAs. Surprisingly, however, addition of C-5 methyl groups to cytosines actually decreases affinity in binding RNA, while the same substitution in DNA is thermally stabilizing. possible sources of this divergent behavior are discussed. A synthesis of 5-methylcytidine ribonucleoside 2'-O-silyl-3'-O-phosphoramidite is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00059-x
• 作为产物：
  描述：

  在 氨 、 碳酸氢钠 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 2',3',5'-tri-O-benzoyl-5-methylcytidine
  参考文献：
  名称：

  Facile methods for the synthesis of 5-formylcytidine

  摘要：

  DOI：

  10.1016/s0040-4039(00)02191-2