(5S,6RS)-1-benzyl-5-benzyloxy-6-hydroxy-2-piperidinone | 1032819-34-3

• 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: (5S,6RS)-1-benzyl-5-benzyloxy-6-hydroxy-2-piperidinone
• 英文别名: (5S)-1-benzyl-6-hydroxy-5-phenylmethoxypiperidin-2-one
• CAS: 1032819-34-3
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: UMHLLRVTQYAFFO-KKFHFHRHSA-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：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  呋喃 、 (5S,6RS)-1-benzyl-5-benzyloxy-6-hydroxy-2-piperidinone 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以71%的产率得到(5S)-1-benzyl-5-benzyloxy-6-(2-furyl)-2-piperidinone
  参考文献：
  名称：

  A new approach for the asymmetric synthesis of (2S,3S)-3-hydroxypipecolic acid

  摘要：

  An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid was achieved from (S)-glutamic acid via the furylation of an N-protected 6-hydroxy-2-piperidinone using furan as a nucleophile and the oxidation of the furyl group to a carboxylic group as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.031
• 作为产物：
  描述：

  (S)-1-benzyl-3-(benzyloxy)piperidine-2,6-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到(5S,6RS)-1-benzyl-5-benzyloxy-6-hydroxy-2-piperidinone
  参考文献：
  名称：

  A new approach for the asymmetric synthesis of (2S,3S)-3-hydroxypipecolic acid

  摘要：

  An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid was achieved from (S)-glutamic acid via the furylation of an N-protected 6-hydroxy-2-piperidinone using furan as a nucleophile and the oxidation of the furyl group to a carboxylic group as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.031

文献信息

• A new approach for the asymmetric synthesis of (2S,3S)-3-hydroxypipecolic acid
  作者：Liang-Xian Liu、Qi-Long Peng、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2008.04.031

  日期：2008.5

  An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid was achieved from (S)-glutamic acid via the furylation of an N-protected 6-hydroxy-2-piperidinone using furan as a nucleophile and the oxidation of the furyl group to a carboxylic group as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.