(R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane | 608136-22-7

• 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)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane
• 英文别名: [(2R)-1-[tert-butyl(dimethyl)silyl]oxy-5-phenylmethoxypentan-2-yl] acetate
• CAS: 608136-22-7
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: YHQVSYMCUUTSQZ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane 在 palladium on activated charcoal 氢气 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 氯仿 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 生成 [(2R)-1-[tert-butyl(dimethyl)silyl]oxy-5-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]pentan-2-yl] acetate
  参考文献：
  名称：

  Lipase TL-Mediated Kinetic Resolution of 5-Benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol at Low Temperature:  Concise Asymmetric Synthesis of Both Enantiomers of a Piperazic Acid Derivative

  摘要：

  Lipase TL-mediated kinetic resolution of (+/-)-5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol (5) at low temperature proceeded to give the corresponding (S)-alcohol 5 and (R)-acetate 6 in quantitative yields with high enantiomeric purity. The addition of bases such as pyridine, DMAP, 2,4- and 2,6-lutidines, or triethylamine considerably enhanced the rate of kinetic resolution. The alcohol (S)-5 and the acetate (R)-6 were converted to piperazic acid derivatives (R)- and (S)-3, respectively, via the intramolecular Mitsunobu reaction as a key step.

  DOI：

  10.1021/jo034441n
• 作为产物：
  描述：

  乙酸乙烯酯 、 (+/-)-5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol 在 4-二甲氨基吡啶 、 Lipase TL(R) 作用下， 以 正己烷 为溶剂， 反应 6.0h， 以54%的产率得到(R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane
  参考文献：
  名称：

  Lipase TL-Mediated Kinetic Resolution of 5-Benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol at Low Temperature:  Concise Asymmetric Synthesis of Both Enantiomers of a Piperazic Acid Derivative

  摘要：

  Lipase TL-mediated kinetic resolution of (+/-)-5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol (5) at low temperature proceeded to give the corresponding (S)-alcohol 5 and (R)-acetate 6 in quantitative yields with high enantiomeric purity. The addition of bases such as pyridine, DMAP, 2,4- and 2,6-lutidines, or triethylamine considerably enhanced the rate of kinetic resolution. The alcohol (S)-5 and the acetate (R)-6 were converted to piperazic acid derivatives (R)- and (S)-3, respectively, via the intramolecular Mitsunobu reaction as a key step.

  DOI：

  10.1021/jo034441n