(3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-phenylacetamido-4-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one | 173105-19-6

• 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: (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-phenylacetamido-4-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• 英文别名: methyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(2S,3S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]butanoate
• CAS: 173105-19-6
• 化学式: C₂₇H₄₂N₂O₇Si
• 分子量: 534.725
• InChiKey: ISQNPRXAXHHDDV-GEPXCNEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-phenylacetamido-4-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以50%的产率得到Potassium; (E)-2-[(2S,3S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoate
  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 碳酸氢钠 、 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 27.0h， 生成 (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-phenylacetamido-4-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
  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