(2R,3S,3aR,7S,7aS)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-3,7a-(epoxymethano)benzofuran-7-yl 4-oxopentanoate | 1453218-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (2R,3S,3aR,7S,7aS)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-3,7a-(epoxymethano)benzofuran-7-yl 4-oxopentanoate
• CAS: 1453218-16-0
• 化学式: C₁₉H₂₄N₂O₈
• 分子量: 408.408
• InChiKey: ZNAIZDPXUXIVIB-IAZQSEGYSA-N

物化性质

• 熔点：
  238-239 °C(Solvent: Dichloromethane)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  136.92
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,3aR,7S,7aS)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-3,7a-(epoxymethano)benzofuran-7-yl 4-oxopentanoate 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N-甲基咪唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以60%的产率得到(2R,3S,3aR,7S,7aS)-3a-(((2-cyanoethoxy)(diisopropylamino)-phosphanyl)oxy)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-3,7a-(epoxymethano)benzofuran-7-yl 4-oxopentanoate
  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：

  1-((2R,3R,3aR,7S,7aS)-3a,7-bis(benzyloxy)-3-hydroxy-7a-((naphthalen-2-ylmethoxy)methyl)octahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 吡啶 、 4-二甲氨基吡啶 、 10 wt% Pd(OH)2 on carbon 、 水 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 137.75h， 生成 (2R,3S,3aR,7S,7aS)-3a-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-3,7a-(epoxymethano)benzofuran-7-yl 4-oxopentanoate
  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