5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-2-methoxy-D-ribonolactone | 1583259-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-2-methoxy-D-ribonolactone
• 英文别名: (3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 1583259-99-7
• 化学式: C₁₉H₃₀O₅Si
• 分子量: 366.53
• InChiKey: XDCKAFRGTBXZLH-BRWVUGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-2-methoxy-D-ribonolactone 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 3.5h， 生成 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-1-deoxy-1a-(3-fluorophenyl)-2-methoxy-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：

  (2R,3S,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-methoxy-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pentanoate 在 2,6-二甲基吡啶 、 水 、 三氟乙酸 、 锌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 74.25h， 生成 5-benzyloxy-3-(tert-butyldimethylsilyl)oxy-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