(2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-(methylsulfonyloxy)tetrahydrofuran-3-yl benzoate | 1583260-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-(methylsulfonyloxy)tetrahydrofuran-3-yl benzoate
• CAS: 1583260-44-9
• 化学式: C₂₀H₂₀F₂O₇S
• 分子量: 442.437
• InChiKey: URXCTOBLZOWKLA-QNZPCDNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-(methylsulfonyloxy)tetrahydrofuran-3-yl benzoate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以377 mg的产率得到(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
• 作为产物：
  描述：

  (3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 在 吡啶 、 溶剂黄146 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 57.0h， 生成 (2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-(methylsulfonyloxy)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