(3R,4S)-4-<1(R)-<(tert-Butyldimethylsilyl)oxy>benzyl>-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one | 153463-35-5

• 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)-4-<1(R)-<(tert-Butyldimethylsilyl)oxy>benzyl>-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (3R,4R)-4-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 153463-35-5
• 化学式: C₂₃H₃₁NO₄Si
• 分子量: 413.589
• InChiKey: YYVNOOAMEHBDGG-NJDAHSKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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)-4-<1(R)-<(tert-Butyldimethylsilyl)oxy>benzyl>-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one 在 吡啶 、 chromium(VI) oxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 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,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone 在 palladium on activated charcoal 咪唑 、 三乙基铝 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 (3R,4S)-4-<1(R)-<(tert-Butyldimethylsilyl)oxy>benzyl>-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
  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

• Asymmetric synthesis of α-keto β-lactams via [2+2] cycloaddition reaction: A concise approach to optically active (α-hydroxy β-lactams and β-alkyl(aryl)isoserines.
  作者：Claudio Palomo、Jesús M. Aizpurua、José I. Miranda、Antonia Mielgo、José M. Odriozola

  DOI：10.1016/s0040-4039(00)73743-9

  日期：1993.9

  The cycloaddition reaction of the Evans-Sjögren ketenes to imines, followed by α-hydroxylation of the resulting cycloadducts provides an efficient general asymmetric synthesis of α-keto β-lactams and derivatives.

  Evans-Sjögren烯酮与亚胺的环加成反应，然后对所得的环加合物进行α-羟基化反应，可有效地进行α-酮基β-内酰胺及其衍生物的一般不对称合成。
• 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.