N4-benzoyl-1-{2-O-{2,3-di-O-acetyl-5-azido-5-deoxy-5-[(trifluoroacetyl)amino]-β-D-ribofuranosyl}-β-D-ribofuranosyl}cytosine | 389063-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N4-benzoyl-1-{2-O-{2,3-di-O-acetyl-5-azido-5-deoxy-5-[(trifluoroacetyl)amino]-β-D-ribofuranosyl}-β-D-ribofuranosyl}cytosine
• 英文别名: N⁴-benzoyl-1-{2-O-{2,3-di-O-acetyl-5-azido-5-deoxy-5-[(trifluoroacetyl)amino]-β-D-ribofuranosyl}-β-D-ribofuranosyl}cytosine
• CAS: 389063-56-3
• 化学式: C₂₇H₂₉F₃N₄O₁₂
• 分子量: 658.542
• InChiKey: XUVFICXJVJKBDE-IWGXDMJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  213.84
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N4-benzoyl-1-{2-O-{2,3-di-O-acetyl-5-azido-5-deoxy-5-[(trifluoroacetyl)amino]-β-D-ribofuranosyl}-β-D-ribofuranosyl}cytosine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 N⁴-benzoyl-1-{2-O-{2,3-di-O-acetyl-5-azido-5-deoxy-5-[(trifluoroacetyl)amino]-β-D-ribofuranosyl}-5-O-(dimethoxytrityl)-β-D-ribofuranosyl}cytosine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Oligonucleotides Containing Disaccharide Nucleosides

  摘要：

  Disaccharide nucleosides with 2'-O-(D-arabinofuranosyl), 2'-O-(L-arabinofuranosyl), 2'-O-(D-ribopyranosyl), 2'-O-(D-erythrofuranosyl), and 2'-O-(5-azido-5-deoxy-D-ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table). Single substitution resulted in a DeltaT(m) of +0.5 to -1.4 degrees for DNA/RNA and a DeltaT(m) of - 0.8 to -4.7 degrees for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH2- C(5") group has a beneficial effect on duplex stability.

  DOI：

  10.1002/1522-2675(20010815)84:8<2387::aid-hlca2387>3.0.co;2-f
• 作为产物：
  描述：

  N4-benzoyl-1-[2-O-(2,3-di-O-acetyl-5-azido-5-deoxy-β-D-ribofuranosyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]cytosine 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.25h， 生成 N4-benzoyl-1-{2-O-{2,3-di-O-acetyl-5-azido-5-deoxy-5-[(trifluoroacetyl)amino]-β-D-ribofuranosyl}-β-D-ribofuranosyl}cytosine
  参考文献：
  名称：

  Oligonucleotides Containing Disaccharide Nucleosides

  摘要：

  Disaccharide nucleosides with 2'-O-(D-arabinofuranosyl), 2'-O-(L-arabinofuranosyl), 2'-O-(D-ribopyranosyl), 2'-O-(D-erythrofuranosyl), and 2'-O-(5-azido-5-deoxy-D-ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table). Single substitution resulted in a DeltaT(m) of +0.5 to -1.4 degrees for DNA/RNA and a DeltaT(m) of - 0.8 to -4.7 degrees for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH2- C(5") group has a beneficial effect on duplex stability.

  DOI：

  10.1002/1522-2675(20010815)84:8<2387::aid-hlca2387>3.0.co;2-f