5'-O-(dimethoxytrityl)-5-carbomethoxymethyl-2-thiouridine | 321991-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(dimethoxytrityl)-5-carbomethoxymethyl-2-thiouridine
• CAS: 321991-60-0
• 化学式: C₃₃H₃₄N₂O₉S
• 分子量: 634.707
• InChiKey: MRVQJTMDCWTPDN-PYXCEVMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  141.47
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5'-O-(dimethoxytrityl)-5-carbomethoxymethyl-2-thiouridine 在 咪唑 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 13.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-carbomethoxymethyl-2-thiouridine-3'-(cyanoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Synthesis and Biophysical Characterization of tRNA^Lys,3 Anticodon Stem-Loop RNAs Containing the mcm⁵s²U Nucleoside

  摘要：

  Phosphoramidite reagents of the naturally occurring modified nucleosides mcm(5)s(2)U and mcm(5)U were synthesized and along with pseudouridine were incorporated into 17-nucleotide lysine tRNA anticodon stem-loop domains. Standard RNA phosphoramidite coupling chemistry allowed us to systematically investigate the thermodynamic effects of nucleoside modification and to correlate thermodynamic trends with qualitative structure effects seen by NMR spectroscopy.

  DOI：

  10.1021/ol006605h
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 5-methoxycarbonylmethyl-2-thiouridine 在 吡啶 作用下， 反应 12.0h， 以80%的产率得到5'-O-(dimethoxytrityl)-5-carbomethoxymethyl-2-thiouridine
  参考文献：
  名称：

  Synthesis and Biophysical Characterization of tRNA^Lys,3 Anticodon Stem-Loop RNAs Containing the mcm⁵s²U Nucleoside

  摘要：

  Phosphoramidite reagents of the naturally occurring modified nucleosides mcm(5)s(2)U and mcm(5)U were synthesized and along with pseudouridine were incorporated into 17-nucleotide lysine tRNA anticodon stem-loop domains. Standard RNA phosphoramidite coupling chemistry allowed us to systematically investigate the thermodynamic effects of nucleoside modification and to correlate thermodynamic trends with qualitative structure effects seen by NMR spectroscopy.

  DOI：

  10.1021/ol006605h