1-<3'-O-acetyl-2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl>-5-methyl-4-(1,2,4-triazolyl)pyrimidine-2(1H)-one | 219706-26-0

• 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-<3'-O-acetyl-2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl>-5-methyl-4-(1,2,4-triazolyl)pyrimidine-2(1H)-one
• CAS: 219706-26-0
• 化学式: C₃₅H₃₅N₅O₇
• 分子量: 637.692
• InChiKey: ARNWLBKDTHGEIU-QAXCHELISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128.82
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-<3'-O-acetyl-2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl>-5-methyl-4-(1,2,4-triazolyl)pyrimidine-2(1H)-one 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 14.0h， 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：

  5'-O-dimethoxytrityl-α-thymidine 在 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 12.5h， 生成 1-<3'-O-acetyl-2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl>-5-methyl-4-(1,2,4-triazolyl)pyrimidine-2(1H)-one
  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