5-(thien-2-yl)-5'-O-(dimethoxytrityl)-2'-deoxyuridine | 155603-87-5

• 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-(thien-2-yl)-5'-O-(dimethoxytrityl)-2'-deoxyuridine
• 英文别名: 5-(thien-2-yl)-2′-deoxyuridine；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-thiophen-2-ylpyrimidine-2,4-dione
• CAS: 155603-87-5
• 化学式: C₃₄H₃₂N₂O₇S
• 分子量: 612.703
• InChiKey: CMDTWVPTHJWZOQ-ILJQZKEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(thien-2-yl)-5'-O-(dimethoxytrityl)-2'-deoxyuridine 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 5-thien-2-yl-1-(β-D-2-deoxyribofuranos-1-yl)uracil
  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：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 5-(thien-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

• Oligodeoxynucleotides Containing Multiple Thiophene-Modified Isomorphic Fluorescent Nucleosides
  作者：Mary S. Noé、Renatus W. Sinkeldam、Yitzhak Tor

  DOI：10.1021/jo4008964

  日期：2013.8.16

  5-(Thien-2-yl)-2'-deoxyuridine, an isomorphic fluorescent nucleoside analogue, was incorporated into multiple positions within single stranded oligodeoxynucleotides. With minimal impact on duplex stability and overall structure, oligonucleotides containing three identical isomorphic fluorescent nucleosides in alternating or neighboring positions display enhanced, sequence-dependent on-signals for either duplex formation or dissociation.
• 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.