5-benzyloxy-3-hydroxy-2-tert-butyl-D-arabinolactone | 1583259-62-4

• 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: 5-benzyloxy-3-hydroxy-2-tert-butyl-D-arabinolactone
• CAS: 1583259-62-4
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: UIQNOLWAQXZPHZ-HZSPNIEDSA-N

物化性质

• 沸点：
  429.0±35.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-3-hydroxy-2-tert-butyl-D-arabinolactone 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以87.5%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：

  3-苄氧基丙醛 在 二异丙氧基二氯化钛 、 CHF₃O₃S*C₁₃H₁₈N₂O 、 水 、 三氟乙酸 、 copper dichloride 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 136.0h， 生成 5-benzyloxy-3-hydroxy-2-tert-butyl-D-arabinolactone
  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