(2S)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-methoxy-2-methyl-3-oxo(113C)propanoic acid | 171963-24-9

• 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: (2S)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-methoxy-2-methyl-3-oxo(113C)propanoic acid
• CAS: 171963-24-9
• 化学式: C₁₆H₂₉NO₆Si
• 分子量: 360.484
• InChiKey: BTHJITIHVNSXGZ-GBWBERTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-methoxy-2-methyl-3-oxo(113C)propanoic acid 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.5h， 生成 bis[tert-butyl(dimethyl)silyl] (2R)-2-[(2S,3S)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-2-methyl(113C)propanedioate
  参考文献：
  名称：

  An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics

  摘要：

  The dramatic difference in reactivity of the two diastereomeric acid esters 4A and 4B during decarboxylation has been thoroughly investigated, The (R) isomer 4A underwent decarboxylation to provide a 94:6 mixture of 5A and 5B at 80 degrees C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 degrees C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products, A mechanistic rationale for this unusual reactivity profile is provided.

  DOI：

  10.1021/jo00131a010
• 作为产物：
  描述：

  二氧化碳-13C 、 (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-(methoxycarbonyl)ethyl>azetidin-2-one 在 lithium diisopropyl amide 作用下， 生成 (2R)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-methoxy-2-methyl-3-oxo(113C)propanoic acid 、 (2S)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-methoxy-2-methyl-3-oxo(113C)propanoic acid
  参考文献：
  名称：

  An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics

  摘要：

  The dramatic difference in reactivity of the two diastereomeric acid esters 4A and 4B during decarboxylation has been thoroughly investigated, The (R) isomer 4A underwent decarboxylation to provide a 94:6 mixture of 5A and 5B at 80 degrees C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 degrees C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products, A mechanistic rationale for this unusual reactivity profile is provided.

  DOI：

  10.1021/jo00131a010

文献信息

• An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics
  作者：Woo-Baeg Choi、Hywyn R. O. Churchill、Joseph E. Lynch、R. P. Volante、Paul J. Reider、Ichiro Shinkai、Deborah K. Jones、Dennis C. Liotta

  DOI：10.1021/jo00131a010

  日期：1995.12

  The dramatic difference in reactivity of the two diastereomeric acid esters 4A and 4B during decarboxylation has been thoroughly investigated, The (R) isomer 4A underwent decarboxylation to provide a 94:6 mixture of 5A and 5B at 80 degrees C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 degrees C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products, A mechanistic rationale for this unusual reactivity profile is provided.