(1'R,3S,4S,4'S)-N-(p-Anisyl)-3-fluoro-3-(1'-hydroxyethyl)-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-azetidinone

• 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: (1'R,3S,4S,4'S)-N-(p-Anisyl)-3-fluoro-3-(1'-hydroxyethyl)-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-azetidinone
• 英文别名: (3S,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-fluoro-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one
• 化学式: C₁₇H₂₂FNO₅
• 分子量: 339.364
• InChiKey: BMLLRUDAUIAINZ-MJRMRKOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3S,4S,4'S)-N-(p-Anisyl)-3-acetyl-3-fluoro-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-azetidinone 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (1'S,3S,4S,4'S)-N-(p-Anisyl)-3-fluoro-3-(1'-hydroxyethyl)-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-azetidinone 、 (1'R,3S,4S,4'S)-N-(p-Anisyl)-3-fluoro-3-(1'-hydroxyethyl)-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-azetidinone
  参考文献：
  名称：

  Stereocontrol by the carbon-fluorine bond and its application to asymmetric synthesis of 3-fluoro .beta.-lactams

  摘要：

  Optically active 3-fluoro-beta-lactams 4 and 5 were prepared via a ketene-imine cycloaddition reaction using fluoroacetyl chloride and an imine derived from (R)-glyceraldehyde acetonide. The high stereoselectivity observed can be rationalized as a consequence of stereoelectronic effects. Deprotonated beta-lactams 4 and 12 were reacted with alkylating agents to give exclusively cis-3-alkyl-substituted derivatives of 3-fluoro beta-lactams. The directed aldol reaction of beta-lactams 4 and 12 with aldehydes and ketones provides cis-3-hydroxyalkyl derivatives with high stereoselectivity; however, diastereoisomeric control was not maintained at the hydroxylated carbon atom. The desired stereochemistry in the side chain was achieved by reduction of 3-acetyl-3-fluoro beta-lactam 22. The lithium enolates of beta-lactams 4 and 12 have been investigated by low-temperature F-19 NMR studies.

  DOI：

  10.1021/jo00061a019

文献信息

• Stereocontrol by the carbon-fluorine bond and its application to asymmetric synthesis of 3-fluoro .beta.-lactams
  作者：John T. Welch、Koichi Araki、Robert Kawecki、John A. Wichtowski

  DOI：10.1021/jo00061a019

  日期：1993.4

  Optically active 3-fluoro-beta-lactams 4 and 5 were prepared via a ketene-imine cycloaddition reaction using fluoroacetyl chloride and an imine derived from (R)-glyceraldehyde acetonide. The high stereoselectivity observed can be rationalized as a consequence of stereoelectronic effects. Deprotonated beta-lactams 4 and 12 were reacted with alkylating agents to give exclusively cis-3-alkyl-substituted derivatives of 3-fluoro beta-lactams. The directed aldol reaction of beta-lactams 4 and 12 with aldehydes and ketones provides cis-3-hydroxyalkyl derivatives with high stereoselectivity; however, diastereoisomeric control was not maintained at the hydroxylated carbon atom. The desired stereochemistry in the side chain was achieved by reduction of 3-acetyl-3-fluoro beta-lactam 22. The lithium enolates of beta-lactams 4 and 12 have been investigated by low-temperature F-19 NMR studies.