tert-butyl N-[(1S)-1-[(2R,3S)-1-benzyl-3-hydroxy-4-oxoazetidin-2-yl]-2-methylpropyl]carbamate | 159611-60-6

• 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: tert-butyl N-[(1S)-1-[(2R,3S)-1-benzyl-3-hydroxy-4-oxoazetidin-2-yl]-2-methylpropyl]carbamate
• CAS: 159611-60-6
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: JQFHVZQTZUUBHT-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-[(2R,3S)-1-benzyl-3-hydroxy-4-oxoazetidin-2-yl]-2-methylpropyl]carbamate 在 phosphorus pentoxide 、 二甲基亚砜 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (4R)-3-benzyl-4-<(1S)-1--2-methylpropyl>oxazolidine-2,5-dione
  参考文献：
  名称：

  New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams

  摘要：

  A conceptually new route for the generation of optically active alpha-aminoacid N-carboxy anhydrides (NCAs) and hence alpha-amino acid derivatives is described. The strategy developed is simple and consists of the oxidation of alpha-hydroxy beta-lactams to the corresponding alpha-keto beta-lactams followed by a Baeyer-Villiger rearrangement. By that means, a wide variety of functionalized alpha-aminoacid N-carboxy anhydrides can be obtained, i.e., alpha,beta-diamino acid and alpha-amino beta-hydroxy acid-derived NCAs. The starting alpha-hydroxy(alkoxy) beta-lactams required for the study are easily prepared in large quantities either by the cycloaddition reaction of achiral alkoxyketenes with chiral aldehyde-derived imines or by the addition of Grignard reagents to a 3-(benzyloxy)-4-formylazetidin-2-one. The construction of a wide variety of NCA's from non-amino acid precursors becomes the most remarkable point of the reaction methodology developed.

  DOI：

  10.1021/jo00090a033
• 作为产物：
  描述：

  tert-butyl N-[(1S)-1-[(2R,3S)-1-benzyl-4-oxo-3-phenylmethoxyazetidin-2-yl]-2-methylpropyl]carbamate 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 生成 tert-butyl N-[(1S)-1-[(2R,3S)-1-benzyl-3-hydroxy-4-oxoazetidin-2-yl]-2-methylpropyl]carbamate
  参考文献：
  名称：

  New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams

  摘要：

  A conceptually new route for the generation of optically active alpha-aminoacid N-carboxy anhydrides (NCAs) and hence alpha-amino acid derivatives is described. The strategy developed is simple and consists of the oxidation of alpha-hydroxy beta-lactams to the corresponding alpha-keto beta-lactams followed by a Baeyer-Villiger rearrangement. By that means, a wide variety of functionalized alpha-aminoacid N-carboxy anhydrides can be obtained, i.e., alpha,beta-diamino acid and alpha-amino beta-hydroxy acid-derived NCAs. The starting alpha-hydroxy(alkoxy) beta-lactams required for the study are easily prepared in large quantities either by the cycloaddition reaction of achiral alkoxyketenes with chiral aldehyde-derived imines or by the addition of Grignard reagents to a 3-(benzyloxy)-4-formylazetidin-2-one. The construction of a wide variety of NCA's from non-amino acid precursors becomes the most remarkable point of the reaction methodology developed.

  DOI：

  10.1021/jo00090a033

文献信息

• New Synthesis of .alpha.-Amino Acid N-Carboxy Anhydrides through Baeyer-Villiger Oxidation of .alpha.-Keto .beta.-Lactams
  作者：Claudio Palomo、Jesus M. Aizpurua、Inaki Ganboa、Francois Carreaux、Carmen Cuevas、Elena Maneiro、Jesus M. Ontoria

  DOI：10.1021/jo00090a033

  日期：1994.6

  A conceptually new route for the generation of optically active alpha-aminoacid N-carboxy anhydrides (NCAs) and hence alpha-amino acid derivatives is described. The strategy developed is simple and consists of the oxidation of alpha-hydroxy beta-lactams to the corresponding alpha-keto beta-lactams followed by a Baeyer-Villiger rearrangement. By that means, a wide variety of functionalized alpha-aminoacid N-carboxy anhydrides can be obtained, i.e., alpha,beta-diamino acid and alpha-amino beta-hydroxy acid-derived NCAs. The starting alpha-hydroxy(alkoxy) beta-lactams required for the study are easily prepared in large quantities either by the cycloaddition reaction of achiral alkoxyketenes with chiral aldehyde-derived imines or by the addition of Grignard reagents to a 3-(benzyloxy)-4-formylazetidin-2-one. The construction of a wide variety of NCA's from non-amino acid precursors becomes the most remarkable point of the reaction methodology developed.
• 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.