(3R,4S)-3-[(1R)-1-(methanesulfonyloxy)ethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one | 927678-33-9

• 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: (3R,4S)-3-[(1R)-1-(methanesulfonyloxy)ethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one
• CAS: 927678-33-9
• 化学式: C₈H₁₅NO₇S₂
• 分子量: 301.342
• InChiKey: IFYAFICPNKHDIT-QYNIQEEDSA-N

物化性质

• 熔点：
  143-145 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  622.9±20.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  115.84
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-[(1R)-1-(methanesulfonyloxy)ethyl]-4-[(methanesulfonyloxy)methyl]azetidin-2-one 、 benzyl 2,3-dioxobutanoate 以15%的产率得到
  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：

  (3R,4S)-3-[(1R)-1-(methanesulfonyloxy)ethyl]-4-[(methanesulfonyloxy)methyl]-1-(4-methoxyphenyl)azetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以66%的产率得到(3R,4S)-3-[(1R)-1-(methanesulfonyloxy)ethyl]-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