(3S,4R)-3-[(1S)-1-acetoxyethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one | 927678-67-9

• 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,4R)-3-[(1S)-1-acetoxyethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one
• CAS: 927678-67-9
• 化学式: C₉H₁₅NO₆S
• 分子量: 265.287
• InChiKey: XDCJWFGNNIXKOI-APQOSEDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  98.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-[(1S)-1-acetoxyethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (6R,7S)-7-((S)-1-Hydroxy-ethyl)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-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：

  benzyl (2R,3S)-3-[(1S)-1-acetoxyethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (3S,4R)-3-[(1S)-1-acetoxyethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one
  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