(3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one | 161871-15-4

• 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,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• 英文别名: methyl (2R,3S)-2-[(2R,3R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-oxo-3-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)azetidin-1-yl]-3-hydroxybutanoate
• CAS: 161871-15-4
• 化学式: C₂₈H₃₀N₂O₈
• 分子量: 522.555
• InChiKey: OXWLRHBNWPYUIH-BDTKHYAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 在 palladium on activated charcoal 氢气 、 三氯化铁 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 25.0 ℃ 、358.53 kPa 条件下， 反应 13.16h， 生成 (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Enantioselective Total Syntheses of [6R,7R] and [6S,7S] Tricyclic β-Lactams

  摘要：

  The reaction of Ox-glycyl chloride with a chiral imine derived from the combination of D-(R)-glyceraldehyde acetonide and protected D-threonine afforded optically active, highly functionalized cis-substituted beta-lactams 11 and 12. These beta-lactams provide versatile intermediates for the syntheses of biologically important carbacephalosporins, isooxacephems, and other multicyclic beta-lactams. Desilylation and oxidation of 12 with Dess-Martin periodinane followed by intramolecular cyclization produced a novel tricyclic beta-lactam 17 and a 1-(hydroxymethyl)-O-2-isocephem 18 with [6R,7R] absolute configuration. Removal of the Ox protecting group and acylation of 17 in a one-pot reaction followed by saponification furnished the target salt 24. Alternatively, reaction of phthaloylglycyl chloride with the chiral imine derived from the combination of L-(S)-glyceraldehyde acetonide and protected D-threonine gave only one enantiomeric azetidinone 27 in high yield. Further manipulation of 27 provided a new tricyclic beta-lactam 39 with [6S,7S] absolute configuration which satisfies the stereochemistry typically required for antibacterial activity, This synthetic procedure provides a short, versatile and enantioselective method of preparing polycyclic beta-lactams. Biological testing of these tricyclic beta-lactams indicated that salt 39 has potential inhibitory activity against four typical strains of bacteria.

  DOI：

  10.1021/jo951651u
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 TEA 、 magnesium sulfate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
  参考文献：
  名称：

  β-内酰胺的不对称合成及其绝对构型的确定

  摘要：

  衍生自D-甘油醛和苏氨酸衍生物的手性亚胺与氧代氯酰氯的反应产生了光学活性的顺式取代的β-内酰胺。关键中间体的绝对构型通过X射线分析和化学降解来确定。

  DOI：

  10.1016/0040-4039(94)02294-l

文献信息

• Asymmetric syntheses of β-lactams and determination of their absolute configuration
  作者：Chuansheng Niu、Marvin J. Miller

  DOI：10.1016/0040-4039(94)02294-l

  日期：1995.1

  Reactions of chiral imines derived from D-glyceraldehyde and threonine derivatives with Oxyglycylchloride gave optically active cis-substituted β-lactams. The absolute configuration of key intermediates were determined by X-ray analysis and chemical degradation.

  衍生自D-甘油醛和苏氨酸衍生物的手性亚胺与氧代氯酰氯的反应产生了光学活性的顺式取代的β-内酰胺。关键中间体的绝对构型通过X射线分析和化学降解来确定。
• Enantioselective Total Syntheses of [6<i>R</i>,7<i>R</i>] and [6<i>S</i>,7<i>S</i>] Tricyclic β-Lactams
  作者：Chuansheng Niu、Teresia Pettersson、Marvin J. Miller

  DOI：10.1021/jo951651u

  日期：1996.1.1

  The reaction of Ox-glycyl chloride with a chiral imine derived from the combination of D-(R)-glyceraldehyde acetonide and protected D-threonine afforded optically active, highly functionalized cis-substituted beta-lactams 11 and 12. These beta-lactams provide versatile intermediates for the syntheses of biologically important carbacephalosporins, isooxacephems, and other multicyclic beta-lactams. Desilylation and oxidation of 12 with Dess-Martin periodinane followed by intramolecular cyclization produced a novel tricyclic beta-lactam 17 and a 1-(hydroxymethyl)-O-2-isocephem 18 with [6R,7R] absolute configuration. Removal of the Ox protecting group and acylation of 17 in a one-pot reaction followed by saponification furnished the target salt 24. Alternatively, reaction of phthaloylglycyl chloride with the chiral imine derived from the combination of L-(S)-glyceraldehyde acetonide and protected D-threonine gave only one enantiomeric azetidinone 27 in high yield. Further manipulation of 27 provided a new tricyclic beta-lactam 39 with [6S,7S] absolute configuration which satisfies the stereochemistry typically required for antibacterial activity, This synthetic procedure provides a short, versatile and enantioselective method of preparing polycyclic beta-lactams. Biological testing of these tricyclic beta-lactams indicated that salt 39 has potential inhibitory activity against four typical strains of bacteria.