1-[5-O-acetyl-2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(2,4,6-trimethylbenzenesulfonyloxy)pyrimidin-2(1H)-one | 242815-21-0

• 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: 1-[5-O-acetyl-2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(2,4,6-trimethylbenzenesulfonyloxy)pyrimidin-2(1H)-one
• CAS: 242815-21-0
• 化学式: C₄₂H₄₄N₂O₁₀S
• 分子量: 768.885
• InChiKey: RAEVPTRGEFMEQI-VYSOZWTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  141.48
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-[5-O-acetyl-2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(2,4,6-trimethylbenzenesulfonyloxy)pyrimidin-2(1H)-one 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 37.0h， 生成 1-[2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(4-phenoxyphenylamino)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Stabilizing a DNA Three-Way Junction by Insertion of N4-Aryl-2-deoxy-5-methylcytidines.

  摘要：

  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.

  DOI：

  10.3891/acta.chem.scand.53-0497
• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 5'-O-acetyl-3'-O-(4,4'-dimethoxytrityl)-α-thymidine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以76%的产率得到1-[5-O-acetyl-2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(2,4,6-trimethylbenzenesulfonyloxy)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Stabilizing a DNA Three-Way Junction by Insertion of N4-Aryl-2-deoxy-5-methylcytidines.

  摘要：

  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.

  DOI：

  10.3891/acta.chem.scand.53-0497