(2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-iodo-tetrahydrofuran-3-yl benzoate | 1583260-45-0

• 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: (2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-iodo-tetrahydrofuran-3-yl benzoate
• CAS: 1583260-45-0
• 化学式: C₁₉H₁₇F₂IO₄
• 分子量: 474.243
• InChiKey: LXJHIZLWIUNNPK-JNIOUFIGSA-N

物化性质

• 沸点：
  487.4±45.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-iodo-tetrahydrofuran-3-yl benzoate 、 N-(三甲基硅基)-2-(三甲基硅氧基)-4-嘧啶胺 在 dipotassium peroxodisulfate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 50.0h， 以60%的产率得到
  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：

  苯甲酰氯 在 吡啶 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 7.0h， 生成 (2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-iodo-tetrahydrofuran-3-yl benzoate
  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