benzyl (3S)-2-acetyloxy-3-[tert-butyl(dimethyl)silyl]oxypiperidine-1-carboxylate | 958447-75-1

• 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 (3S)-2-acetyloxy-3-[tert-butyl(dimethyl)silyl]oxypiperidine-1-carboxylate
• CAS: 958447-75-1
• 化学式: C₂₁H₃₃NO₅Si
• 分子量: 407.582
• InChiKey: ZIRRKFFLTBPVKV-OYKVQYDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (3S)-2-acetyloxy-3-[tert-butyl(dimethyl)silyl]oxypiperidine-1-carboxylate 、 1-(三甲基硅氧基)环戊烯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到C₂₄H₃₇NO₄Si
  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
• 作为产物：
  描述：

  C₁₉H₃₁NO₄Si 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl (3S)-2-acetyloxy-3-[tert-butyl(dimethyl)silyl]oxypiperidine-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