benzyl N-[(4R)-5-[tert-butyl(dimethyl)silyl]oxy-4-hydroxypentyl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbamate | 608136-30-7

• 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: benzyl N-[(4R)-5-[tert-butyl(dimethyl)silyl]oxy-4-hydroxypentyl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbamate
• CAS: 608136-30-7
• 化学式: C₂₄H₄₂N₂O₆Si
• 分子量: 482.693
• InChiKey: ZMXMFIMPWUZDKI-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(4R)-5-[tert-butyl(dimethyl)silyl]oxy-4-hydroxypentyl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbamate 在 chromium(VI) oxide 、 硫酸 、 四丁基氟化铵 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 4.67h， 生成 methyl (S)-1-benzyloxycarbonylhexahydropyridazine-3-carboxylate
  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：

  (R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane 在 palladium on activated charcoal 水 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 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 8.0h， 生成 benzyl N-[(4R)-5-[tert-butyl(dimethyl)silyl]oxy-4-hydroxypentyl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbamate
  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

文献信息

• Lipase TL-Mediated Kinetic Resolution of 5-Benzyloxy-1-<i>tert</i>-butyldimethylsilyloxy-2-pentanol at Low Temperature:  Concise Asymmetric Synthesis of Both Enantiomers of a Piperazic Acid Derivative
  作者：Yutaka Aoyagi、Yoshihiro Saitoh、Tasuku Ueno、Mai Horiguchi、Koichi Takeya、Robert M. Williams

  DOI：10.1021/jo034441n

  日期：2003.9.1

  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.