{(S)-1-[(2R,3S)-3-Hydroxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-3-methyl-butyl}-carbamic acid tert-butyl ester | 144260-75-3

• 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)-1-[(2R,3S)-3-Hydroxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-3-methyl-butyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S)-1-[(2R,3S)-3-hydroxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]-3-methylbutyl]carbamate
• CAS: 144260-75-3
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: ZMNQSOSLZKOQID-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  88.1
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(2R,3S)-3-Hydroxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-3-methyl-butyl}-carbamic acid tert-butyl ester 在 chromium trioxide-pyridine complex 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 tert-butyl N-[(1S)-1-[(2R,3S)-3-hydroxy-1-(4-methoxyphenyl)-3-methyl-4-oxoazetidin-2-yl]-3-methylbutyl]carbamate
  参考文献：
  名称：

  Stereocontrolled synthesis of 3,5-dialkyl-4-amino pyrrolidin-2-ones from β-lactams as chiral templates.

  摘要：

  A new approach to 3,5-dialkyl pyrrolidin-2-ones by intramolecular rearrangemen

  DOI：

  10.1016/s0040-4039(00)61296-0
• 作为产物：
  描述：

  {(S)-1-[(2R,3S)-3-Benzyloxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-3-methyl-butyl}-carbamic acid tert-butyl ester 在 palladium on activated charcoal ammonium formate 作用下， 以80%的产率得到{(S)-1-[(2R,3S)-3-Hydroxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-3-methyl-butyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Palomo, Claudio; Cossio, Fernando P.; Cuevas, Carmen, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 7, p. 541 - 554

  摘要：

  DOI：

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.