(1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester | 173241-47-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester
• 英文别名: methyl (1R,2S,3S,6R,7S)-7-methyl-4-oxo-3-[(2-phenylacetyl)amino]-8,10-dioxa-5-azatricyclo[5.2.1.02,5]decane-6-carboxylate
• CAS: 173241-47-9
• 化学式: C₁₈H₂₀N₂O₆
• 分子量: 360.367
• InChiKey: BAZDYBYIYGOHMF-HMZURLEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以93%的产率得到Potassium; (1R,2S,3S,6R,7S)-7-methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylate
  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：

  (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amino}-butyric acid methyl ester 在 silica gel 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 一水合肼 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 126.92h， 生成 (1R,2S,3S,6R,7S)-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

文献信息

• 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.