3'-O-ethyl-4'-C-(hydroxymethyl)thymidine | 161016-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-O-ethyl-4'-C-(hydroxymethyl)thymidine
• 英文别名: 1-[(2R,4S)-4-ethoxy-5,5-bis(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 161016-60-0
• 化学式: C₁₃H₂₀N₂O₆
• 分子量: 300.312
• InChiKey: KKYKHLHCROHYJM-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  113.78
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3'-O-ethyl-4'-C-(hydroxymethyl)thymidine 在 氨 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 18.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-ethyl-4'-C-(hydroxymethyl)thymidine
  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：

  5'-O-tritylthymidine 在 吡啶 、 氢氧化钾 、 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 1,4-二氧六环 、 甲醇 、 二甲基亚砜 、 苯 为溶剂， 反应 61.0h， 生成 3'-O-ethyl-4'-C-(hydroxymethyl)thymidine
  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