(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-one | 1583259-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-one
• CAS: 1583259-54-4
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: ORRHDUXSOZSFAA-UOWFLXDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-benzyloxy-3-hydroxy-2-methoxy-D-ribonolactone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 (3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-one
  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