1-((1S,3R,4S)-3-(benzyloxy)-4-((benzyloxy)methyl)cyclopentyl)-5-fluoropyrimidine-2,4(1H,3H)-dione | 1061362-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((1S,3R,4S)-3-(benzyloxy)-4-((benzyloxy)methyl)cyclopentyl)-5-fluoropyrimidine-2,4(1H,3H)-dione
• CAS: 1061362-67-1
• 化学式: C₂₄H₂₅FN₂O₄
• 分子量: 424.472
• InChiKey: NEUJRHAWSILTEQ-JAXLGGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-((1S,3R,4S)-3-(benzyloxy)-4-((benzyloxy)methyl)cyclopentyl)-5-fluoropyrimidine-2,4(1H,3H)-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (+/-)-5-fluoro-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)-cyclopentyl>-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Cyclopentane-Nucleobase Coupling in the Synthesis of Carbocyclic L-Nucleosides: is A S _N 2-Reaction an Alternative to the Mitsunobu-Reaction?

  摘要：

  Several carbocyclic L-nucleosides have been synthesized by coupling a cyclopentane-system with heterocycles according to a modified Mitsunobu-protocol. This reaction gave two regioisomers, the NI-alkylated product and an unwanted O-2-product. A simple, S(N)2-reaction has been investigated as an alternative for such couplings.

  DOI：

  10.1080/15257770701527745
• 作为产物：
  描述：

  (1R,3R,4S)-3-(benzyloxy)-4-((benzyloxy)methyl)cyclopentyl methanesulfonate 、 N3-BZ-5-氟尿嘧啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以14%的产率得到1-((1S,3R,4S)-3-(benzyloxy)-4-((benzyloxy)methyl)cyclopentyl)-5-fluoropyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Cyclopentane-Nucleobase Coupling in the Synthesis of Carbocyclic L-Nucleosides: is A S _N 2-Reaction an Alternative to the Mitsunobu-Reaction?

  摘要：

  Several carbocyclic L-nucleosides have been synthesized by coupling a cyclopentane-system with heterocycles according to a modified Mitsunobu-protocol. This reaction gave two regioisomers, the NI-alkylated product and an unwanted O-2-product. A simple, S(N)2-reaction has been investigated as an alternative for such couplings.

  DOI：

  10.1080/15257770701527745