(2R,3S,4R)-isopropyl 2-allyl-5-(benzyloxy)-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate | 1583259-44-2

• 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: (2R,3S,4R)-isopropyl 2-allyl-5-(benzyloxy)-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate
• CAS: 1583259-44-2
• 化学式: C₂₇H₄₃NO₅
• 分子量: 461.642
• InChiKey: RUFRRBMKMZSAJY-SMIHKQSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-苄氧基-1-丙醇 在 二异丙氧基二氯化钛 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid 、 copper dichloride 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 56.0h， 生成 (2R,3S,4R)-isopropyl 2-allyl-5-(benzyloxy)-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 、 (2S,3S,4R)-isopropyl 2-allyl-5-(benzyloxy)-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate
  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