(+)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]cytosine | 330805-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (+)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]cytosine
• CAS: 330805-89-5
• 化学式: C₁₆H₂₈FN₃O₂Si
• 分子量: 341.501
• InChiKey: IZODMTGNGRAXHB-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  70.14
• 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,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]cytosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到(-)-1-[(1S,4S)-4-fluoro-4-hydroxymethylcyclopentan-1-yl]cytosine
  参考文献：
  名称：

  A divergent synthesis of d - and l -carbocyclic 4′-fluoro-2′,3′-dideoxynucleosides as potential antiviral agents

  摘要：

  D- and L-Carbocyclic 4'-fluoro-2',3'-dideoxynucleosides have been synthesized from 2, which can be conveniently prepared from 1.2:5.6-di-O-isopropylidene-D-mannitol 1 in eight steps. Ruthenium-catalyzed ring-closing metathesis has been employed in the synthesis of D-nucleosides, whereas the L-series have been obtained through an intramolecular nucleophilic substitution reaction. The Mitsunobu condensation was used as a general tool for the synthesis of both purine and pyrimidine nucleosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00482-1
• 作为产物：
  描述：

  (-)-(1S,3S)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol 在 吡啶 、 1H-1,2,4-三唑 、 lithium aluminium tetrahydride 、 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 、 4-氯苯基二氯磷酸酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (+)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]cytosine
  参考文献：
  名称：

  A divergent synthesis of d - and l -carbocyclic 4′-fluoro-2′,3′-dideoxynucleosides as potential antiviral agents

  摘要：

  D- and L-Carbocyclic 4'-fluoro-2',3'-dideoxynucleosides have been synthesized from 2, which can be conveniently prepared from 1.2:5.6-di-O-isopropylidene-D-mannitol 1 in eight steps. Ruthenium-catalyzed ring-closing metathesis has been employed in the synthesis of D-nucleosides, whereas the L-series have been obtained through an intramolecular nucleophilic substitution reaction. The Mitsunobu condensation was used as a general tool for the synthesis of both purine and pyrimidine nucleosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00482-1