1-[(2R,4aR,7S,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3-benzoyl-5-methylpyrimidine-2,4-dione | 193559-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-[(2R,4aR,7S,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3-benzoyl-5-methylpyrimidine-2,4-dione
• CAS: 193559-25-0
• 化学式: C₂₅H₂₄N₂O₆
• 分子量: 448.475
• InChiKey: KQQRIDHEKSEEML-VMIIQTFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,4aR,7S,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3-benzoyl-5-methylpyrimidine-2,4-dione 在 氨 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 1,5-Anhydro-2,3-dideoxy2-(thymin-1-yl)-D-arabinohexitol
  参考文献：
  名称：

  Hexitol Nucleic Acids (HNA): Synthesis and Properties

  摘要：

  While improved alkylation procedures have been worked out for the coupling of purine bases to the anhydrohexitol ring using sulphonate activating groups on the anhydrohexitol ring, the Mitsunobu reaction seems to be the method of choice for synthesis of the pyrimidine analogues. In a mixed sequence context, the anhydrohexitol oligonucleotides still display strong and very selective basepairing properties, with a strong preference for RNA as the complement.

  DOI：

  10.1080/07328319708006119
• 作为产物：
  描述：

  N-3-benzoylthymine 、 1',5'-anhydro-4,6-O-benzylidene-3-deoxy-D-glucitol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到1-[(2R,4aR,7S,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3-benzoyl-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Hexitol Nucleic Acids (HNA): Synthesis and Properties

  摘要：

  While improved alkylation procedures have been worked out for the coupling of purine bases to the anhydrohexitol ring using sulphonate activating groups on the anhydrohexitol ring, the Mitsunobu reaction seems to be the method of choice for synthesis of the pyrimidine analogues. In a mixed sequence context, the anhydrohexitol oligonucleotides still display strong and very selective basepairing properties, with a strong preference for RNA as the complement.

  DOI：

  10.1080/07328319708006119

文献信息

• Hexitol Nucleic Acids (HNA): Synthesis and Properties
  作者：B. De Bouvere、L. Kerreinans、C. Hendrix、H. De Winter、G. Schepers、A. Van Aerschot、P. Herdewijn

  DOI：10.1080/07328319708006119

  日期：1997.7

  While improved alkylation procedures have been worked out for the coupling of purine bases to the anhydrohexitol ring using sulphonate activating groups on the anhydrohexitol ring, the Mitsunobu reaction seems to be the method of choice for synthesis of the pyrimidine analogues. In a mixed sequence context, the anhydrohexitol oligonucleotides still display strong and very selective basepairing properties, with a strong preference for RNA as the complement.