(2S,3S,4R)-3-Hydroxy-2-((S)-hydroxy-phenyl-methyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid | 184965-05-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3S,4R)-3-Hydroxy-2-((S)-hydroxy-phenyl-methyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid
• CAS: 184965-05-7
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: QUCULJYKNATUCU-BDXNGKNPSA-N

物化性质

• 沸点：
  595.8±50.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106.86
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-3-Hydroxy-2-((S)-hydroxy-phenyl-methyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid 在 四(三苯基膦)钯 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 甲酸:三乙胺 1:1 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Stereochemical Change in the Lewis Acid-promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue

  摘要：

  In the presence of BF3 . OEt2, the reaction of (3R)-5-t-butyldimethylsiloxy-6-methyl-3-phenyl-1H-pyrrol[1,2-c]oxazole (3) with aliphatic aldehydes in ether occurred stereoselectively to give the corresponding (3R, 7aR, 1'R)-isomers (4a and 6a) as the major products, while the similar reaction with aromatic aldehydes afforded the (3R, 7aR, 1'S)-isomers (7b, 8b, and 9b) predominantly. The product (7b) from the reaction with benzaldehyde was successfully transformed to a lactacystin analogue.

  DOI：

  10.3987/com-98-8123
• 作为产物：
  描述：

  (3R,6R,7S,7aS)-7-Hydroxy-7a-((S)-hydroxy-phenyl-methyl)-6-methyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 在 盐酸 、 sodium hydroxide 、 jones' reagent 、 氢氟酸 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 (2S,3S,4R)-3-Hydroxy-2-((S)-hydroxy-phenyl-methyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Stereochemical Change in the Lewis Acid-promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue

  摘要：

  In the presence of BF3 . OEt2, the reaction of (3R)-5-t-butyldimethylsiloxy-6-methyl-3-phenyl-1H-pyrrol[1,2-c]oxazole (3) with aliphatic aldehydes in ether occurred stereoselectively to give the corresponding (3R, 7aR, 1'R)-isomers (4a and 6a) as the major products, while the similar reaction with aromatic aldehydes afforded the (3R, 7aR, 1'S)-isomers (7b, 8b, and 9b) predominantly. The product (7b) from the reaction with benzaldehyde was successfully transformed to a lactacystin analogue.

  DOI：

  10.3987/com-98-8123