N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide | 1583260-54-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide
• 英文别名: N-[1-[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-fluoro-3-methyl-5-(phenylmethoxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 1583260-54-1
• 化学式: C₃₀H₃₈FN₃O₅Si
• 分子量: 567.733
• InChiKey: IFQFDYGBMYNEFQ-YZFHNSIOSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 在 盐酸 、 三氯化硼 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(1-((2R,3R,4R,5R)-3-氟-4-羟基-5-(羟甲基)-3-甲基四氢呋喃-2-
  参考文献：
  名称：

  A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir

  摘要：

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

  DOI：

  10.1021/ja502205q
• 作为产物：
  描述：

  N4-苯甲酰基胞嘧啶 在 ammonium sulfate 、 四氯化锡 作用下， 以 氯苯 为溶剂， 反应 17.0h， 生成 N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 、 N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide
  参考文献：
  名称：

  A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir

  摘要：

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

  DOI：

  10.1021/ja502205q