9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(1,2,4-triazol-4-yl)purine | 163632-55-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(1,2,4-triazol-4-yl)purine
• 英文别名: 9-(2-deoxy-β-D-erythro-pentofuranose)-6-(1,2,4-triazol-4-yl)purine；N⁶-(1,2,4-triazole-4-yl)-2'-deoxyadenosine；6-(1,2,4-triazol-4-yl)purine 2'-deoxyribonucleoside；(2R,3S,5R)-2-(hydroxymethyl)-5-[6-(1,2,4-triazol-4-yl)purin-9-yl]oxolan-3-ol
• CAS: 163632-55-1
• 化学式: C₁₂H₁₃N₇O₃
• 分子量: 303.28
• InChiKey: WEXQXHOINIOUFQ-DJLDLDEBSA-N

物化性质

• 沸点：
  695.4±65.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(1,2,4-triazol-4-yl)purine 以 吡啶 为溶剂， 生成 5'-O-dimethoxytrityl-6-N-(5-azapentane-1-yl)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of Polyaminooligonucleotides and Their Combinatorial Libraries

  摘要：

  A synthesis of phosphoramidites of 2'-deqxyadenosine and 2'-deoxyguanosine carrying a protected spermine moiety at N-6 and N-2 positions respectively is described. An approach to analyse properties of polyaminooligonucleotides using their synthetic combinatorial libraries is described and discussed. A synthesis of a polyaminooligonucleotide combinatorial library was carried out and the analysis of the library clearly showed that the presence of spermine moieties in oligodeoxyribonucleotides increases stability of their complexes.

  DOI：

  10.1080/07328319908044749
• 作为产物：
  描述：

  N,N'-bis(dimethylaminomethylene)hydrazine 、 2'-脱氧腺苷 在 吡啶 、 三甲基氯硅烷 、 甲醇 作用下， 反应 27.0h， 以62%的产率得到9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(1,2,4-triazol-4-yl)purine
  参考文献：
  名称：

  [用于带有带有反应性残基的接头的寡核苷酸合成的单体：I。在杂环碱基中具有甲氧基草酰胺基的脱氧核苷衍生物的合成]。

  摘要：

  制备了用于标准亚磷酰胺寡脱氧核苷酸合成的许多单体，这些单体带有连接到胸苷，2'-脱氧胞苷和2'-脱氧腺苷杂环碱基上的反应性甲氧基草酰胺基。该论文的英文版：Russian Journal of Bioorganic Chemistry，2004年，第1卷。30号 3; 另请参见http://www.maik.ru。

  DOI：

  10.1023/b:rubi.0000030129.13466.18

文献信息

• Miles, Robert W.; Samano, Vicente; Robins, Morris J., Journal of the American Chemical Society, 1995, vol. 117, # 22, p. 5951 - 5957
  作者：Miles, Robert W.、Samano, Vicente、Robins, Morris J.

  DOI：——

  日期：——
• Synthetic Oligonucleotide Combinatorial Libraries. 3. Synthesis of Polyamevonucleosides
  作者：Przemyslaw Godzina、Katarzyna Adrych-Rozek、Wojciech T. Markiewicz

  DOI：10.1080/07328319908044615

  日期：1999.11

  Synthesis of polyamino-2'-deoxynucleosides was studied. A synthesis of 2'-deoxyadenosine and 2'-deoxyguanosine derivatives carrying a protected spermine moiety at N-6 and N-2 positions respectively is described using unprotected polyamines as substrates. The question of reactivity of primary and secondary amino groups present in polyamines was studied. The evidence that only primary amino groups react with the synthesised precursors was accomplished from experiments with a secondary amine (di-n-butylamine). An approach to analyse properties of polyaminooligonucleotides using their synthetic combinatorial libraries is discussed.