(S)-1-((2S,3S,3aS,9aR)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(naphthalen-2-ylmethoxy)-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-2-yl)but-3-en-1-yl acetate | 1453217-85-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-1-((2S,3S,3aS,9aR)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(naphthalen-2-ylmethoxy)-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-2-yl)but-3-en-1-yl acetate
• CAS: 1453217-85-0
• 化学式: C₄₂H₄₄N₂O₇Si
• 分子量: 716.906
• InChiKey: CZCPYOKWKFFCMB-RUWNGRLASA-N

物化性质

• 沸点：
  752.3±70.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  52.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.11
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((2S,3S,3aS,9aR)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(naphthalen-2-ylmethoxy)-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-2-yl)but-3-en-1-yl acetate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以0.536 g的产率得到(S)-1-((2S,3S,3aS,9aR)-2-(Hydroxymethyl)-3-(naphthalen-2-ylmethoxy)-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2′,3′:4,5]oxazolo[3,2-a]pyrimidin-2-yl)but-3-en-1-yl acetate
  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 、 N,O-双三甲硅基乙酰胺 、 水 、 potassium carbonate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 62.0h， 生成 (S)-1-((2S,3S,3aS,9aR)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(naphthalen-2-ylmethoxy)-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-2-yl)but-3-en-1-yl acetate
  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