5-<1-(N,N-dimethylsulfamoyl)imidazol-2-yl>-5'-O-(dimethoxytrityl)-2'-deoxyuridine | 155603-88-6

• 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-<1-(N,N-dimethylsulfamoyl)imidazol-2-yl>-5'-O-(dimethoxytrityl)-2'-deoxyuridine
• 英文别名: 2-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-N,N-dimethylimidazole-1-sulfonamide
• CAS: 155603-88-6
• 化学式: C₃₅H₃₇N₅O₉S
• 分子量: 703.773
• InChiKey: NVHGSRIBTNRHBG-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-<1-(N,N-dimethylsulfamoyl)imidazol-2-yl>-5'-O-(dimethoxytrityl)-2'-deoxyuridine 在 sodium hydroxide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 49.5h， 生成 5-(imidazol-2-yl)-2'-deoxyuridine
  参考文献：
  名称：

  5-Heteroaryl-2'-deoxyuridine Analogs. Synthesis and Incorporation into High-Affinity Oligonucleotides

  摘要：

  A series of C-5 heteroaryl-2'-deoxyuridines were synthesized from 5-iodo-2'-deoxyuridine. Palladium catalyzed coupling with heteroarylstannanes proved to be a convenient and general method of preparation. Oligonucleotides containing pyridine-, thiophene-, thiazole-, and imidazole-substituted 2'-deoxyuridine analogs gave enhanced thermal stability to complementary RNA relative to thymidine. Thermal denaturation studies showed that oligodeoxynucleotides (ODNs) containing 5-(thiazol-2-yl)-2'-deoxyuridine exhibit the highest thermal denaturation (Tm) and therefore may increase the potency of these ODNs to inhibit gene expression in a sequence specific manner.

  DOI：

  10.1021/ja00092a003
• 作为产物：
  描述：

  4-Methyl-benzoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[5-iodo-3-(4-methyl-benzoyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 silver(l) oxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 5-<1-(N,N-dimethylsulfamoyl)imidazol-2-yl>-5'-O-(dimethoxytrityl)-2'-deoxyuridine
  参考文献：
  名称：

  5-Heteroaryl-2'-deoxyuridine Analogs. Synthesis and Incorporation into High-Affinity Oligonucleotides

  摘要：

  A series of C-5 heteroaryl-2'-deoxyuridines were synthesized from 5-iodo-2'-deoxyuridine. Palladium catalyzed coupling with heteroarylstannanes proved to be a convenient and general method of preparation. Oligonucleotides containing pyridine-, thiophene-, thiazole-, and imidazole-substituted 2'-deoxyuridine analogs gave enhanced thermal stability to complementary RNA relative to thymidine. Thermal denaturation studies showed that oligodeoxynucleotides (ODNs) containing 5-(thiazol-2-yl)-2'-deoxyuridine exhibit the highest thermal denaturation (Tm) and therefore may increase the potency of these ODNs to inhibit gene expression in a sequence specific manner.

  DOI：

  10.1021/ja00092a003

文献信息

• 5-Heteroaryl-2'-deoxyuridine Analogs. Synthesis and Incorporation into High-Affinity Oligonucleotides
  作者：Arnold J. Gutierrez、Terry J. Terhorst、Mark D. Matteucci、Brian C. Froehler

  DOI：10.1021/ja00092a003

  日期：1994.6

  A series of C-5 heteroaryl-2'-deoxyuridines were synthesized from 5-iodo-2'-deoxyuridine. Palladium catalyzed coupling with heteroarylstannanes proved to be a convenient and general method of preparation. Oligonucleotides containing pyridine-, thiophene-, thiazole-, and imidazole-substituted 2'-deoxyuridine analogs gave enhanced thermal stability to complementary RNA relative to thymidine. Thermal denaturation studies showed that oligodeoxynucleotides (ODNs) containing 5-(thiazol-2-yl)-2'-deoxyuridine exhibit the highest thermal denaturation (Tm) and therefore may increase the potency of these ODNs to inhibit gene expression in a sequence specific manner.