5'-O-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-5,6-dimethyluridine | 268745-99-9

• 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-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-5,6-dimethyluridine
• 英文别名: 1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyoxolan-2-yl]-5,6-dimethylpyrimidine-2,4-dione
• CAS: 268745-99-9
• 化学式: C₃₈H₄₈N₂O₈Si
• 分子量: 688.893
• InChiKey: QJJQRQUUJLKRQF-DYICDNQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 5'-O-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-5,6-dimethyluridine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到5'-O-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-5,6-dimethyluridine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis and Properties of Uniquely Modified Oligoribonucleotides: Yeast Trna^PheFragments with 6-Methyluridine and 5,6-Dimethyluridine at Site-Specific Positions

  摘要：

  The phosphoramidites of 6-methyluridine and 5,6-dimethyluridine were synthesized and the modified uridines site-selectively incorporated into heptadecamers corresponding in sequence to the yeast tRNA(Phe) anticodon and T Psi C domains. The oligoribonucleotides were characterized by NMR, MALDI-TOF MS and UV-monitored thermal denaturations. The 6-methylated uridines retained the syn conformation at the polymer level and in each sequence location destabilized the RNAs compared to that of the unmodified RNA. The decrease in RNA duplex stability is predictable. However, loss of stability when the modified uridine is in a loop is sequence context dependent, and can not, at this time, be predicted from the location in the loop.

  DOI：

  10.1080/15257770008035004
• 作为产物：
  描述：

  1-β-D-ribofuranosyl-5,6-dimethyluracil 在 吡啶 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 生成 5'-O-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-5,6-dimethyluridine
  参考文献：
  名称：

  Synthesis and Properties of Uniquely Modified Oligoribonucleotides: Yeast Trna^PheFragments with 6-Methyluridine and 5,6-Dimethyluridine at Site-Specific Positions

  摘要：

  The phosphoramidites of 6-methyluridine and 5,6-dimethyluridine were synthesized and the modified uridines site-selectively incorporated into heptadecamers corresponding in sequence to the yeast tRNA(Phe) anticodon and T Psi C domains. The oligoribonucleotides were characterized by NMR, MALDI-TOF MS and UV-monitored thermal denaturations. The 6-methylated uridines retained the syn conformation at the polymer level and in each sequence location destabilized the RNAs compared to that of the unmodified RNA. The decrease in RNA duplex stability is predictable. However, loss of stability when the modified uridine is in a loop is sequence context dependent, and can not, at this time, be predicted from the location in the loop.

  DOI：

  10.1080/15257770008035004