3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-α-thymidine | 219706-25-9

• 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: 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-α-thymidine
• CAS: 219706-25-9
• 化学式: C₃₃H₃₄N₂O₈
• 分子量: 586.642
• InChiKey: VINVRLVGJSZQQZ-JBOQNHBVSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118.08
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-α-thymidine 在 ammonium hydroxide 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 吡啶 、 乙腈 为溶剂， 反应 17.5h， 生成 3'-O-acetyl-N4-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-α-cytidine
  参考文献：
  名称：

  Improved Targeting of the Flanks of a DNA Stem Using α-Oligodeoxynucleotides.-The Enhanced Effect of an Intercalator

  摘要：

  2'-Deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)-alpha-cytidine (5) was prepared by reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)-alpha-thymidine derivative 3 which was synthesized from 5-O-DMT protected alpha-thymidine 1. Aminolysis of 3 afforded 3'-O-acetyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-alpha-cytidine (8). Benzoylation of 8 and removal of acetyl afforded N-4-benzoyl-(2)-deoxy-5-O-(4,4'-dimethoxytrityl)-5-methyl-alpha-cytidine (10). The amidites of compounds 5 and 10 were prepared and used in ol-oligonucleotide synthesis. DNA three-way junction (TWJ) is stabilized when an alpha-ODN is used for targeting the dangling flanks of the stem in a DNA hairpin. Further stabilization of the TWJ is observed when 5 is inserted into the alpha-ODN at the junction region.

  DOI：

  10.1080/07328319808004323
• 作为产物：
  描述：

  乙酸酐 、 5'-O-dimethoxytrityl-α-thymidine 以 吡啶 为溶剂， 以92%的产率得到3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-α-thymidine
  参考文献：
  名称：

  Improved Targeting of the Flanks of a DNA Stem Using α-Oligodeoxynucleotides.-The Enhanced Effect of an Intercalator

  摘要：

  2'-Deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)-alpha-cytidine (5) was prepared by reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)-alpha-thymidine derivative 3 which was synthesized from 5-O-DMT protected alpha-thymidine 1. Aminolysis of 3 afforded 3'-O-acetyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-alpha-cytidine (8). Benzoylation of 8 and removal of acetyl afforded N-4-benzoyl-(2)-deoxy-5-O-(4,4'-dimethoxytrityl)-5-methyl-alpha-cytidine (10). The amidites of compounds 5 and 10 were prepared and used in ol-oligonucleotide synthesis. DNA three-way junction (TWJ) is stabilized when an alpha-ODN is used for targeting the dangling flanks of the stem in a DNA hairpin. Further stabilization of the TWJ is observed when 5 is inserted into the alpha-ODN at the junction region.

  DOI：

  10.1080/07328319808004323

文献信息

• Stabilizing a DNA Three-Way Junction by Insertion of N4-Aryl-2-deoxy-5-methylcytidines.
  作者：Omar M. Ali、Erik B. Pedersen、Anna Lövqvist、Vladimir Tolmachev、Bengt Långström、Shi-Ping Yan、Geng-Lin Wang、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0497

  日期：——

  4,4'-Dimethoxytrityl and acetyl sugar protected alpha and beta thymidines are converted into the corresponding N-4-aryl-2-deoxy-5-methylcytidines via 4-(2,4,6-trimethylbenzenesulfonyloxy) pyrimidin-2(1H)-one nucleosides. These compounds were used for DNA synthesis after deacetylation and phosphitylation. Increased melting temperatures (6.2-9.6 degrees C) of three-way junctions (TWJ) were observed when N-4-(2-anilinophenyl)-, N-4-(2-benzylphenyl)- or N-4-(2-fluorenyl)-2-deoxy-5-methylcytidines were inserted into the middle of the junction region. A 26.6 degrees C increase in melting temperature was observed using a nucleosides in one of the strands of TWJ and with insertion of 2-deoxy-N-4-(2-fluorenyl)-5-methyl-alpha-cytidine at the junction. A large increase in thermal melting (18.8 degrees C) of the TWJ was also observed when 2-deoxy-5-methyl-N-4-(4-phenoxyphenyl)-alpha-cytidine was inserted at the junction as a chimeric nucleoside into a strand of beta nucleosides.