(3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-phthalimido-4-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one | 173105-12-9

• 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-phthalimido-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]-3-(1,3-dioxoisoindol-2-yl)-4-oxoazetidin-1-yl]butanoate
• CAS: 173105-12-9
• 化学式: C₂₇H₃₈N₂O₈Si
• 分子量: 546.693
• InChiKey: OSFIYIYXUUWWEH-FSIJUFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

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-phthalimido-4-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 在 氢氧化钾 、 碳酸氢钠 、 一水合肼 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 24.75h， 生成 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：

  叔丁基二甲基氯硅烷 在 咪唑 、 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-phthalimido-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

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.