4'-C-(benzoyloxymethyl)-3'-O-ethylthymidine | 161016-61-1

• 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'-C-(benzoyloxymethyl)-3'-O-ethylthymidine
• CAS: 161016-61-1
• 化学式: C₂₀H₂₄N₂O₇
• 分子量: 404.42
• InChiKey: QBSBVYDOHDPCQI-YRNRMSPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119.85
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4'-C-(benzoyloxymethyl)-3'-O-ethylthymidine 在 氨 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 4'-C--5'-O-(4,4'-dimethoxytrityl)-3'-O-ethylthymidine
  参考文献：
  名称：

  Synthesis and Evaluation of Oligodeoxynucleotides Containing 3′-O-Ethyl-4′-C-(hydroxymethyl)thymidine: Introduction of a Novel Class of Phosphodiester Internucleoside Linkages

  摘要：

  3'-O-Ethyl-4'-C-(hydroxymethyl)thymidine (5) was synthesized and converted into the phosphoramidite building block 8. Novel oligodeoxynucleotide analogues containing 4'-C-hydroxymethyl phosphodiester internucleoside linkages were synthesized on an automated DNA-synthesizer. The hybridization properties and enzymatic stability were studied on oligomers with one to four modifications. The 3'-end modified oligodeoxynucleotides were resistent towards 3'-exonuclease degradation and showed only moderate lowered affinity towards complementary DNA compared with oligodeoxynucleotides bearing modifications in the middle.

  DOI：

  10.1080/15257779408010674
• 作为产物：
  描述：

  3'-O-ethylthymidine 在 吡啶 、 sodium hydroxide 、 草酸 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 二甲基亚砜 为溶剂， 反应 52.0h， 生成 4'-C-(benzoyloxymethyl)-3'-O-ethylthymidine
  参考文献：
  名称：

  Synthesis and Evaluation of Oligodeoxynucleotides Containing 3′-O-Ethyl-4′-C-(hydroxymethyl)thymidine: Introduction of a Novel Class of Phosphodiester Internucleoside Linkages

  摘要：

  3'-O-Ethyl-4'-C-(hydroxymethyl)thymidine (5) was synthesized and converted into the phosphoramidite building block 8. Novel oligodeoxynucleotide analogues containing 4'-C-hydroxymethyl phosphodiester internucleoside linkages were synthesized on an automated DNA-synthesizer. The hybridization properties and enzymatic stability were studied on oligomers with one to four modifications. The 3'-end modified oligodeoxynucleotides were resistent towards 3'-exonuclease degradation and showed only moderate lowered affinity towards complementary DNA compared with oligodeoxynucleotides bearing modifications in the middle.

  DOI：

  10.1080/15257779408010674