3'-deoxy-3'-(1H-tetrazol-5-yl)thymidine | 497068-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-deoxy-3'-(1H-tetrazol-5-yl)thymidine
• 英文别名: 1-[(2R,4R,5S)-5-(hydroxymethyl)-4-(2H-tetrazol-5-yl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 497068-96-9
• 化学式: C₁₁H₁₄N₆O₄
• 分子量: 294.27
• InChiKey: UYLVPKCUOMTIFR-XLPZGREQSA-N

物化性质

• 密度：
  1.532±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-(1H-tetrazol-5-yl)thymidine 在 三乙胺 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 3'-deoxy-3'-(2-{5'-deoxy-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]thymidin-5'-yl}-2H-tetrazol-5-yl)-5'-O-(4,4'-dimethoxytrityl)thymidine
  参考文献：
  名称：

  摘要：

  Thymidine dimers in which the natural phosphodiester linkage has been replaced by a 2,5-disubstituted tetrazole ring are synthesized and incorporated into oligodeoxynucleotides (ODNs). The synthesis is accomplished by two strategies based on an alkylation of 5'-O-trityl-on and 5'-O-trityl-off 3'-deoxy-3'-(1H-tetrazol-5-vl)thymidines with 5'-iodo-5'-deoxythymidine in the presence of Et3N. and the formation of only 2-substituted tetrazol-5-yl linkages is observed in 89 and 46% yields. respectively. The nucleoside dimer formed is reacted with 4,4'-dimethoxytrityl chloride (DMTCI), followed by treatment with 2-cyanoethyl tetraisopropyl-phosphordiamidite in the presence of NN-diisopropylammonium tetrazolide, to afford the 5'-O-DMT-protecteci dinucleoside phosphoramidite that is used for incorporation into ODNs on an automated DNA synthesizer. The modified ODNs with one and up to five tetrazole internucleosidic linkages are obtained in good yields. The thermal stability of DNA/DNA and DNA/RNA duplexes is studied by UV experiments and reported also.

  DOI：

  10.1002/1522-2675(200209)85:9<2847::aid-hlca2847>3.0.co;2-1
• 作为产物：
  描述：

  1-(3'-cyano-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine 在 dimethyl ammonium azide 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 3'-deoxy-3'-(1H-tetrazol-5-yl)thymidine
  参考文献：
  名称：

  摘要：

  Thymidine dimers in which the natural phosphodiester linkage has been replaced by a 2,5-disubstituted tetrazole ring are synthesized and incorporated into oligodeoxynucleotides (ODNs). The synthesis is accomplished by two strategies based on an alkylation of 5'-O-trityl-on and 5'-O-trityl-off 3'-deoxy-3'-(1H-tetrazol-5-vl)thymidines with 5'-iodo-5'-deoxythymidine in the presence of Et3N. and the formation of only 2-substituted tetrazol-5-yl linkages is observed in 89 and 46% yields. respectively. The nucleoside dimer formed is reacted with 4,4'-dimethoxytrityl chloride (DMTCI), followed by treatment with 2-cyanoethyl tetraisopropyl-phosphordiamidite in the presence of NN-diisopropylammonium tetrazolide, to afford the 5'-O-DMT-protecteci dinucleoside phosphoramidite that is used for incorporation into ODNs on an automated DNA synthesizer. The modified ODNs with one and up to five tetrazole internucleosidic linkages are obtained in good yields. The thermal stability of DNA/DNA and DNA/RNA duplexes is studied by UV experiments and reported also.

  DOI：

  10.1002/1522-2675(200209)85:9<2847::aid-hlca2847>3.0.co;2-1