(3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2(3H)-one | 1583260-50-7

• 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: (3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2(3H)-one
• 英文别名: (3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-fluoro-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 1583260-50-7
• 化学式: C₁₉H₂₉FO₄Si
• 分子量: 368.521
• InChiKey: SBNPODUBXKOSDN-GPMSIDNRSA-N

物化性质

• 沸点：
  416.0±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2(3H)-one 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氯化硼 、 四氯化锡 、 二异丁基氢化铝 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯苯 、 甲苯 为溶剂， 反应 18.0h， 生成 N-(1-((2R,3R,4R,5R)-3-氟-4-羟基-5-(羟甲基)-3-甲基四氢呋喃-2-
  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-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal 在 2,6-二甲基吡啶 、 二异丙氧基二氯化钛 、 水 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 47.25h， 生成 (3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2(3H)-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