(S)-2-((2R,3S)-1-Benzyl-3-benzyloxy-4-oxo-azetidin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester | 178208-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (S)-2-((2R,3S)-1-Benzyl-3-benzyloxy-4-oxo-azetidin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[(2R,3S)-1-benzyl-4-oxo-3-phenylmethoxyazetidin-2-yl]piperidine-1-carboxylate
• CAS: 178208-00-9
• 化学式: C₂₇H₃₄N₂O₄
• 分子量: 450.578
• InChiKey: ZKSWHTMGKXXOMD-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((2R,3S)-1-Benzyl-3-benzyloxy-4-oxo-azetidin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 氢气 、 碳酸氢钠 、 potassium bromide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 (4R)-3-benzyl-4-[(2S)-N-(tert-butoxycarbonyl)piperidin-2-yl]oxazolidine-2,5-dione
  参考文献：
  名称：

  Generation of Threonine- and Azathreonine N-Carboxy Anhydrides from α-Hydroxy β-Lactams Promoted by 2,2,6,6-Tetramethylpiperidinyl-1-oxyl (TEMPO) in Combination with Sodium Hypochlorite

  摘要：

  A versatile one-pot oxidation-Baeyer-Villiger reaction sequence applied to alpha-hydroxy beta-lactams and promoted by 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) leads to alpha-amino acid N-carboxy anhydrides. The examples reported constitute the first application of TEMPO in a Baeyer-Villiger reaction and provide a way for peptide coupling from non alpha-amino acid precursors.

  DOI：

  10.1021/jo952178n
• 作为产物：
  描述：

  苄氧基乙酰氯 、 (S)-2-[(E)-Benzylimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以70%的产率得到(S)-2-((2R,3S)-1-Benzyl-3-benzyloxy-4-oxo-azetidin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Generation of Threonine- and Azathreonine N-Carboxy Anhydrides from α-Hydroxy β-Lactams Promoted by 2,2,6,6-Tetramethylpiperidinyl-1-oxyl (TEMPO) in Combination with Sodium Hypochlorite

  摘要：

  A versatile one-pot oxidation-Baeyer-Villiger reaction sequence applied to alpha-hydroxy beta-lactams and promoted by 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) leads to alpha-amino acid N-carboxy anhydrides. The examples reported constitute the first application of TEMPO in a Baeyer-Villiger reaction and provide a way for peptide coupling from non alpha-amino acid precursors.

  DOI：

  10.1021/jo952178n

文献信息

• Generation of Threonine- and Azathreonine <i>N</i>-Carboxy Anhydrides from α-Hydroxy β-Lactams Promoted by 2,2,6,6-Tetramethylpiperidinyl-1-oxyl (TEMPO) in Combination with Sodium Hypochlorite
  作者：Claudio Palomo、Jesús M. Aizpurua、Carmen Cuevas、Raquel Urchegui、Anthony Linden

  DOI：10.1021/jo952178n

  日期：1996.1.1

  A versatile one-pot oxidation-Baeyer-Villiger reaction sequence applied to alpha-hydroxy beta-lactams and promoted by 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) leads to alpha-amino acid N-carboxy anhydrides. The examples reported constitute the first application of TEMPO in a Baeyer-Villiger reaction and provide a way for peptide coupling from non alpha-amino acid precursors.