1-[((1R,2S,3S,5R)-2,3-dihydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl]pyrimidine-2,4(1H,3H)-dione | 1239953-54-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[((1R,2S,3S,5R)-2,3-dihydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl]pyrimidine-2,4(1H,3H)-dione
• CAS: 1239953-54-8
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: KOSZKGVIXYZNOM-DLVJRCHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.11
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.58
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (1R,2S,5R)-6,6-dimethylspiro[bicycle[3.1.1]heptane-2,2’-oxiran]-3-ol 、 尿嘧啶 在 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 以49%的产率得到1-[((1R,2S,3S,5R)-2,3-dihydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

  摘要：

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.054