N⁴-benzoyl-1-[2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-ribofuranosyl]cytosine | 389063-43-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-benzoyl-1-[2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-β-D-ribofuranosyl]cytosine
• 英文别名: [(2S,3S,4R,5S)-5-[(2R,3R,4R,5R)-2-(4-benzamido-2-oxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 389063-43-8
• 化学式: C₄₂H₃₇N₃O₁₃
• 分子量: 791.768
• InChiKey: KYMNGZJHIREUBS-XZTKKZCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  211.04
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N⁴-benzoyl-1-[2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-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-[5-O-(dimethoxytrityl)-2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-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：

  1-O-acetyl-2,3,5-tri-O-benzoyl-L-arabinofuranose 在 四丁基氟化铵 、 四氯化锡 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 29.25h， 生成 N⁴-benzoyl-1-[2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-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