(2R,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(4-methoxyphenyl)amino>-3-phenylpropan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(4-methoxyphenyl)amino>-3-phenylpropan-1-ol
• 英文别名: (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(4-methoxyanilino)-3-phenylpropan-1-ol
• 化学式: C₂₂H₃₃NO₃Si
• 分子量: 387.594
• InChiKey: BDSQLLJQKLPSAL-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S)-4-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-3-(4-methoxyphenyl)-1,3-oxazolidine-2,5-dione 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 21.5h， 生成 (2R,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(4-methoxyphenyl)amino>-3-phenylpropan-1-ol
  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.