dibenzyl (3S)-3-[(1S)-1-acetoxyethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2,2-dicarboxylate | 927678-60-2

• 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: dibenzyl (3S)-3-[(1S)-1-acetoxyethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2,2-dicarboxylate
• CAS: 927678-60-2
• 化学式: C₃₀H₂₉NO₈
• 分子量: 531.562
• InChiKey: AUBYCXMOMSIKQK-FNZWTVRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dibenzyl (3S)-3-[(1S)-1-acetoxyethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2,2-dicarboxylate 在 吡啶 、 sodium hydroxide 作用下， 生成 (3S)-3-[(1S)-1-acetoxyethyl]-2-(benzyloxycarbonyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry

  摘要：

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.034
• 作为产物：
  描述：

  dibenzyl [(4-methoxyphenyl)amino]malonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 生成 dibenzyl (3S)-3-[(1S)-1-acetoxyethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry

  摘要：

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.034