2-[1,2-dideoxy-5-O-(4,4’-dimethoxytrityl)-β-D-ribofuranos-1-yl]-N-(prop-2-ynyl)ethanamide | 1560714-71-7

• 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: 2-[1,2-dideoxy-5-O-(4,4’-dimethoxytrityl)-β-D-ribofuranos-1-yl]-N-(prop-2-ynyl)ethanamide
• CAS: 1560714-71-7
• 化学式: C₃₁H₃₃NO₆
• 分子量: 515.606
• InChiKey: XOZBAMZGHYJBNI-SSBOKUKZSA-N

物化性质

• 沸点：
  718.5±60.0 °C(predicted)
• 密度：
  1.190±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[1,2-dideoxy-5-O-(4,4’-dimethoxytrityl)-β-D-ribofuranos-1-yl]-N-(prop-2-ynyl)ethanamide 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-1-yl}-N-(prop-2-ynyl)ethanamide
  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
• 作为产物：
  描述：

  ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate 在 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 2-[1,2-dideoxy-5-O-(4,4’-dimethoxytrityl)-β-D-ribofuranos-1-yl]-N-(prop-2-ynyl)ethanamide
  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