benzyl (1-((2R,3R,4R,5R)-4-(((benzyloxy)carbonyl)oxy)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate | 1315584-55-4

• 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: benzyl (1-((2R,3R,4R,5R)-4-(((benzyloxy)carbonyl)oxy)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate
• CAS: 1315584-55-4
• 化学式: C₂₆H₂₆FN₃O₈
• 分子量: 527.506
• InChiKey: PGDOCUACLPKIBC-RKCWLVDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  138.21
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl (1-((2R,3R,4R,5R)-4-(((benzyloxy)carbonyl)oxy)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate 、 (2S)-2-((氯(苯氧基)膦)氨基)丙酸乙酯 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到
  参考文献：
  名称：

  Efficient synthesis of nucleoside aryloxy phosphoramidate prodrugs utilizing benzyloxycarbonyl protection

  摘要：

  An efficient method for the synthesis of nucleoside phosphoramidates prodrugs (6a-f) has been developed that employs a simple protection/deprotection sequence of the nucleoside with benzyloxycarbonyl (Cbz). The coupling reaction of Cbz-protected derivatives (5a-f) with phenyl-(ethoxy-L-alaninyl)-phosphorochloridate (7), followed by Cbz group removal by hydrogenolysis provided the phenyl phosphoramidate ProTides (6a-f) in excellent overall yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.046
• 作为产物：
  描述：

  4-amino-1-((2R,3R,4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-fluoro-4-hydroxy-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one 在 4-二甲氨基吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 benzyl (1-((2R,3R,4R,5R)-4-(((benzyloxy)carbonyl)oxy)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate
  参考文献：
  名称：

  Efficient synthesis of nucleoside aryloxy phosphoramidate prodrugs utilizing benzyloxycarbonyl protection

  摘要：

  An efficient method for the synthesis of nucleoside phosphoramidates prodrugs (6a-f) has been developed that employs a simple protection/deprotection sequence of the nucleoside with benzyloxycarbonyl (Cbz). The coupling reaction of Cbz-protected derivatives (5a-f) with phenyl-(ethoxy-L-alaninyl)-phosphorochloridate (7), followed by Cbz group removal by hydrogenolysis provided the phenyl phosphoramidate ProTides (6a-f) in excellent overall yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.046