(4S,5R)-5-(benzyloxymethyl)-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one | 1583260-26-7

• 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: (4S,5R)-5-(benzyloxymethyl)-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one
• CAS: 1583260-26-7
• 化学式: C₂₁H₃₄O₄Si
• 分子量: 378.584
• InChiKey: WVDFEWRIBDMQFF-VQTJNVASSA-N

物化性质

• 沸点：
  448.2±35.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-(benzyloxymethyl)-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one 在 N-氟代双苯磺酰胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以72%的产率得到(3S,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-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
• 作为产物：
  描述：

  3-苄氧基丙醛 在 咪唑 、 4-二甲氨基吡啶 、 二异丙氧基二氯化钛 、 三氟化硼乙醚 、 (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 96.0h， 生成 (4S,5R)-5-(benzyloxymethyl)-4-(triisopropylsilyloxy)dihydrofuran-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