benzyl (2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-prop-2-enylpiperidine-1-carboxylate | 1174147-49-9

• 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 (2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-prop-2-enylpiperidine-1-carboxylate
• CAS: 1174147-49-9
• 化学式: C₂₂H₃₅NO₃Si
• 分子量: 389.61
• InChiKey: YWKFOVJWEIYSPU-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl (3S)-2-acetyloxy-3-[tert-butyl(dimethyl)silyl]oxypiperidine-1-carboxylate 、 烯丙基三甲基锡烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl (2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-prop-2-enylpiperidine-1-carboxylate 、 benzyl (2R,3S)-2-allyl-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate
  参考文献：
  名称：

  BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine

  摘要：

  The asymmetric BF3 center dot Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution. In addition, N,O-acetal 10 was synthesized from L-benzyl glutamate in 11 steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.097

文献信息

• BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine
  作者：Ru-Cheng Liu、Wei Huang、Jing-Yi Ma、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1016/j.tetlet.2009.04.097

  日期：2009.7

  The asymmetric BF3 center dot Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution. In addition, N,O-acetal 10 was synthesized from L-benzyl glutamate in 11 steps. (C) 2009 Elsevier Ltd. All rights reserved.