(3R,4S)-3-(Benzyloxy)-4-<(R)-1-hydroxybenzyl>-1-(4-methoxyphenyl)azetidin-2-one | 159700-12-6

• 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: (3R,4S)-3-(Benzyloxy)-4-<(R)-1-hydroxybenzyl>-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (3R,4S)-4-[(R)-hydroxy(phenyl)methyl]-1-(4-methoxyphenyl)-3-phenylmethoxyazetidin-2-one
• CAS: 159700-12-6
• 化学式: C₂₄H₂₃NO₄
• 分子量: 389.451
• InChiKey: WYILIGBRHVZFLG-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-(Benzyloxy)-4-<(R)-1-hydroxybenzyl>-1-(4-methoxyphenyl)azetidin-2-one 在 palladium on activated charcoal 吡啶 、 咪唑 、 chromium(VI) oxide 、 ammonium formate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (4S)-4-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-3-(4-methoxyphenyl)-1,3-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：

  (3R,4S)-3-(Benzyloxy)-4-<(R)-1-<(tert-butyldimethylsilyl)oxy>benzyl>-1-(4-methoxyphenyl)azetidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到(3R,4S)-3-(Benzyloxy)-4-<(R)-1-hydroxybenzyl>-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  β-内酰胺与格氏试剂的反应选择性合成肾素抑制剂的（syn，anti）-1-氨基-2,3-二醇亚单位

  摘要：

  的新方法BOC保护的氨基二醇1A经由3,4-的开口顺二取代β内酰胺3用异丁基氯化镁进行说明。非外消旋β-内酰胺3可以通过3-乙酰氧基-β-内酰胺4的酶促拆分或从手性前体甲基（R）-（-）-扁桃酸酯获得。

  DOI：

  10.1016/0040-4039(95)00824-v

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.
• Enantioselective synthesis of the (syn,anti)-1-amino-2,3-diol subunit of renin inhibitors by reaction of β-Lactams with a Grignard reagent
  作者：Denice M Spero、Suresh Kapadia、Vittorio Farina

  DOI：10.1016/0040-4039(95)00824-v

  日期：1995.6

  A new approach to the BOC-protected amino diol 1avia the opening of 3,4-cis-disubstituted β-lactam 3 with isobutylmagnesium chloride is described. Nonracemic β-lactam 3 could be obtained by enzymatic resolution of the 3-acetoxy-β-lactam 4 or from a chiral precursor, methyl (R)-(−)-mandelate.

  的新方法BOC保护的氨基二醇1A经由3,4-的开口顺二取代β内酰胺3用异丁基氯化镁进行说明。非外消旋β-内酰胺3可以通过3-乙酰氧基-β-内酰胺4的酶促拆分或从手性前体甲基（R）-（-）-扁桃酸酯获得。