N⁴-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-β-D-ribofuranosyl]cytosine | 389063-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N⁴-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-β-D-ribofuranosyl]cytosine
• 英文别名: [(2R,3R,4S,5R)-5-[[(6aR,8R,9R,9aR)-8-(4-benzamido-2-oxopyrimidin-1-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxy]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 389063-38-1
• 化学式: C₅₄H₆₃N₃O₁₄Si₂
• 分子量: 1034.28
• InChiKey: RYWPVHKIBGCOBO-QIVKCKFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.77
• 重原子数：
  73.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  198.27
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  N⁴-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-β-D-ribofuranosyl]cytosine 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 生成 N⁴-benzoyl-1-[5-O-(dimethoxytrityl)-2-O-(2,3,5-tri-O-benzoyl-α-D-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
• 作为产物：
  描述：

  1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose 、 N4-苯甲酰-3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷二基)胞啶 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 26.0h， 以83%的产率得到N⁴-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-α-D-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