Acetic acid (S)-((2S,3S,4R)-3-acetoxy-4-methyl-5-oxo-2-triethylsilanyloxymethyl-pyrrolidin-2-yl)-phenyl-methyl ester | 208706-94-9

• 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: Acetic acid (S)-((2S,3S,4R)-3-acetoxy-4-methyl-5-oxo-2-triethylsilanyloxymethyl-pyrrolidin-2-yl)-phenyl-methyl ester
• CAS: 208706-94-9
• 化学式: C₂₃H₃₅NO₆Si
• 分子量: 449.62
• InChiKey: RBVNCXZXRSQSMV-UXYIHQQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-((2S,3S,4R)-3-acetoxy-4-methyl-5-oxo-2-triethylsilanyloxymethyl-pyrrolidin-2-yl)-phenyl-methyl ester 在 sodium hydroxide 、 四(三苯基膦)钯 、 jones' reagent 、 氢氟酸 、 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 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