N-[7-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-acetamide | 214833-22-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[7-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-acetamide
• CAS: 214833-22-4
• 化学式: C₁₃H₁₅IN₄O₄
• 分子量: 418.191
• InChiKey: JLHIVTNQWALBGY-IVZWLZJFSA-N

物化性质

• 沸点：
  733.050±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  2.129±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  109.5
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[7-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-acetamide 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-{7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-acetamide
  参考文献：
  名称：

  PHOSPHORAMIDITES AND OLIGONUCLEOTIDES CONTAINING 7-DEAZAPURINES AND PYRIMIDINES CARRYING AMINOPROPARGYL SIDE CHAINS

  摘要：

  The synthesis of phosphoramidites containing 7-deazaguanine, 7-deazaadenine, uracil and cytosine carrying aminopropargyl chains is described. The corresponding oligonucleotides are stabilized in duplexes thermally as well as against degradation by exonucleases.

  DOI：

  10.1081/ncn-100002568
• 作为产物：
  描述：

  5-碘-2'-脱氧结核菌素 在 吡啶 、 氨 、 水 作用下， 反应 2.83h， 生成 N-[7-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-acetamide
  参考文献：
  名称：

  7-Deazaadenine-DNA: Bulky 7-Iodo Substituents or Hydrophobic 7-Hexynyl Chains Are Well Accommodated in the Major Groove of Oligonucleotide Duplexes

  摘要：

  Oligonucleotides containing 7-deaza-7-(hex-1-ynyl)-2'-deoxyadenosine (1) and 7-deaza-7-iodo-2'-deoxyadenosine (2) are described. The corresponding phosphoramidites (3 a,b) were synthesized and employed in solid-phase oligonucleotide synthesis. The modified 7-deazaadenine residues show selective base-pairing with dT. According to the T-m values and the thermodynamic data of duplex formation, the 7-iodo and the 7-(hex-1-ynyl) residues of a 7-deazaadenine moiety increase the duplex stability with retention of the particular DNA structure. This is different from 8-substituted adenine, which destabilizes the nucleic acid duplex significantly. The nucleoside 1 fluoresces strongly.

  DOI：

  10.1002/(sici)1521-3765(19980904)4:9<1781::aid-chem1781>3.0.co;2-k