5-benzyloxy-3-hydroxy-2-methoxy-D-ribonolactone | 1583259-53-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzyloxy-3-hydroxy-2-methoxy-D-ribonolactone
• CAS: 1583259-53-3
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: MIPYYSQCYNMKHH-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-3-hydroxy-2-methoxy-D-ribonolactone 在 2,6-二甲基吡啶 、 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-2-methoxy-1a-(quinolin-3-yl)-α-D-ribofuranose
  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 、 (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid 、 水 、 三氟乙酸 、 copper dichloride 、 锌 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 112.0h， 生成 5-benzyloxy-3-hydroxy-2-methoxy-D-ribonolactone
  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