(3R,4S)-3-[(1R)-1-acetoxyethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one | 927678-48-6

• 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: (3R,4S)-3-[(1R)-1-acetoxyethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one
• CAS: 927678-48-6
• 化学式: C₉H₁₅NO₆S
• 分子量: 265.287
• InChiKey: XDCJWFGNNIXKOI-NJUXHZRNSA-N

物化性质

• 熔点：
  104 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  489.9±10.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

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：

  (3R,4S)-3-[(1R)-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， 反应 5.0h， 生成 (6S,7R)-7-((R)-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：

  dibenzyl {[(2S,3R)-3-acetoxy-2-bromobutyryl](4-methoxyphenyl)amino}malonate 在 palladium on activated charcoal 吡啶 、 碳酸甲丙酯 、 sodium hydroxide 、 ammonium cerium(IV) nitrate 、 氢气 、 氯甲酸乙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 35.83h， 生成 (3R,4S)-3-[(1R)-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