(2S,5S)-tert-butyl 5-hydroxy-2-((S)-2-hydroxy-2-phenylethyl)piperidine-1-carboxylate | 1047679-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,5S)-tert-butyl 5-hydroxy-2-((S)-2-hydroxy-2-phenylethyl)piperidine-1-carboxylate
• 英文别名: tert-butyl (2S,5S)-5-hydroxy-2-[(2S)-2-hydroxy-2-phenylethyl]piperidine-1-carboxylate
• CAS: 1047679-77-5
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: DQLPJPIFHDZONA-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S)-tert-butyl 5-hydroxy-2-((S)-2-hydroxy-2-phenylethyl)piperidine-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到(-)-5-hydroxysedamine
  参考文献：
  名称：

  Asymmetric syntheses of (−)-epi-pseudoconhydrine and (−)-5-hydroxysedamine based on a cis-diastereoselective 1,4-asymmetric induction

  摘要：

  The asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine are reported. The key to these syntheses is an unusual highly cis-diastereoselective 1,4-asymmetric induction in the alpha-amidoallylation of the new chiral building block 15. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.002
• 作为产物：
  描述：

  (3S,6S)-1-(4-methoxybenzyl)-6-((S)-2-hydroxy-2-phenylethyl)piperidin-3-ol 、 二碳酸二叔丁酯 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 以64%的产率得到(2S,5S)-tert-butyl 5-hydroxy-2-((S)-2-hydroxy-2-phenylethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Asymmetric syntheses of (−)-epi-pseudoconhydrine and (−)-5-hydroxysedamine based on a cis-diastereoselective 1,4-asymmetric induction

  摘要：

  The asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine are reported. The key to these syntheses is an unusual highly cis-diastereoselective 1,4-asymmetric induction in the alpha-amidoallylation of the new chiral building block 15. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.002

文献信息

• Asymmetric syntheses of (−)-epi-pseudoconhydrine and (−)-5-hydroxysedamine based on a cis-diastereoselective 1,4-asymmetric induction
  作者：Gang Liu、Jie Meng、Chen-Guo Feng、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2008.05.002

  日期：2008.6

  The asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine are reported. The key to these syntheses is an unusual highly cis-diastereoselective 1,4-asymmetric induction in the alpha-amidoallylation of the new chiral building block 15. (C) 2008 Elsevier Ltd. All rights reserved.