(3R,6R,7S,7aS)-7-Hydroxy-7a-((S)-hydroxy-phenyl-methyl)-6-methyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one | 208706-92-7

• 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: (3R,6R,7S,7aS)-7-Hydroxy-7a-((S)-hydroxy-phenyl-methyl)-6-methyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
• CAS: 208706-92-7
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: OKYKKXNSXVRCEN-HFFHYZHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70.0
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 Acetic acid (S)-((2S,3S,4R)-3-acetoxy-4-methyl-5-oxo-2-triethylsilanyloxymethyl-pyrrolidin-2-yl)-phenyl-methyl ester
  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：

  (R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-3-phenyl-1H-pyrrolo[1,2-c]oxazole 在 四氧化锇 、 N-甲基吲哚酮 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 作用下， 生成 (3R,6R,7S,7aS)-7-Hydroxy-7a-((S)-hydroxy-phenyl-methyl)-6-methyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
  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