(R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal | 1583259-07-7

• 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: (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal
• 英文别名: (2R)-3-phenylmethoxy-2-(2,2,6,6-tetramethylpiperidin-1-yl)oxypropanal
• CAS: 1583259-07-7
• 化学式: C₁₉H₂₉NO₃
• 分子量: 319.444
• InChiKey: YPHOKNJTNLSWML-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 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：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-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 、 三氟乙酸 、 锌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 90.25h， 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
• 作为产物：
  描述：

  溴甲苯 在 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 、 sodium hydride 、 copper dichloride 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 56.5h， 生成 (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal
  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