(6R,7R)-7-((S)-1-Hydroxy-ethyl)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester | 927678-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6R,7R)-7-((S)-1-Hydroxy-ethyl)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• CAS: 927678-27-1
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: LIBKPCVSDZNEEZ-BPNCWPANSA-N

物化性质

• 熔点：
  94-95 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  499.3±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-7-((S)-1-Hydroxy-ethyl)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到(6R,7R)-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 (αR,6R,7R)-7-(1-acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylate 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 (6R,7R)-7-((S)-1-Hydroxy-ethyl)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
  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