(3R,4S,5S)-5-((S)-1-acetoxybut-3-en-1-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-(naphthalen-2-ylmethoxy)tetrahydrofuran-2,3-diyl diacetate | 1453217-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,4S,5S)-5-((S)-1-acetoxybut-3-en-1-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-(naphthalen-2-ylmethoxy)tetrahydrofuran-2,3-diyl diacetate
• CAS: 1453217-81-6
• 化学式: C₄₂H₄₈O₉Si
• 分子量: 724.923
• InChiKey: ZFJZSXSSHYIFGO-UOVNDWSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  52.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-5-((S)-1-acetoxybut-3-en-1-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-(naphthalen-2-ylmethoxy)tetrahydrofuran-2,3-diyl diacetate 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 95.0h， 生成 1-((1S,3R,4S,7S)-1-((S)-1-hydroxybut-3-en-1-yl)-7-(naphthalen-2-ylmethoxy)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  A Constrained Tricyclic Nucleic Acid Analogue of α-l-LNA: Investigating the Effects of Dual Conformational Restriction on Duplex Thermal Stability

  摘要：

  A constrained tricyclic analogue of alpha-L-LNA (2), which contains dual modes of conformational restriction about the ribose sugar moiety, has been synthesized and characterized by X-ray crystallography. Thermal denaturation experiments of oligonucleotide sequences containing this tricyclic alpha-L-LNA analogue (alpha-L-TriNA 2, 5) indicate that this modification is moderately stabilizing when paired with complementary DNA and RNA, but less stabilizing than both alpha-L-LNA (2) and alpha-L-TriNA 1 (4).

  DOI：

  10.1021/jo401170y
• 作为产物：
  描述：

  (S)-1-((3aR,5S,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-ol 在 吡啶 、 水 、 溶剂黄146 作用下， 反应 39.0h， 生成 (3R,4S,5S)-5-((S)-1-acetoxybut-3-en-1-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-(naphthalen-2-ylmethoxy)tetrahydrofuran-2,3-diyl diacetate
  参考文献：
  名称：

  A Constrained Tricyclic Nucleic Acid Analogue of α-l-LNA: Investigating the Effects of Dual Conformational Restriction on Duplex Thermal Stability

  摘要：

  A constrained tricyclic analogue of alpha-L-LNA (2), which contains dual modes of conformational restriction about the ribose sugar moiety, has been synthesized and characterized by X-ray crystallography. Thermal denaturation experiments of oligonucleotide sequences containing this tricyclic alpha-L-LNA analogue (alpha-L-TriNA 2, 5) indicate that this modification is moderately stabilizing when paired with complementary DNA and RNA, but less stabilizing than both alpha-L-LNA (2) and alpha-L-TriNA 1 (4).

  DOI：

  10.1021/jo401170y