3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-1-(prop-2-ynyl)-β-D-ribofuranose | 1560714-69-3

• 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: 3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-1-(prop-2-ynyl)-β-D-ribofuranose
• 英文别名: 3-[[(2R,3S,5S)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-prop-2-ynyloxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 1560714-69-3
• 化学式: C₃₈H₄₇N₂O₆P
• 分子量: 658.775
• InChiKey: XKKBJLQIWJONPC-GGBFTYGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate 在 二异丁基氢化铝 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-1-(prop-2-ynyl)-β-D-ribofuranose
  参考文献：
  名称：

  The Ability of 1-Aryltriazole-Containing Nucleobases to Recognize a TA Base Pair in Triplex DNA

  摘要：

  Phosphoramidites bearing propargyl and (N-propargylcarbamoyl)methyl groups at the Cl-position of deoxyribose were synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various aryl azides led to triplex-forming oligonucleotides (TFOs) possessing the corresponding aryltriazole-containing nucleobases. The triplex-forming ability of TFOs with double-stranded DNA (dsDNA) was evaluated through UV-melting experiments, and it was demonstrated that m-hydroxy or m-ureido derivatives in the (1-aryltriazol-4-yl)methyl nucleobases likely interacted with a TA base pair in dsDNA.

  DOI：

  10.3987/com-13-s(s)33