(3S,4R,5R)-1-benzyl-3,4,5-triacetoxypyrrolidin-2-one | 155397-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4R,5R)-1-benzyl-3,4,5-triacetoxypyrrolidin-2-one
• 英文别名: (2R,3R,4S)-1-Benzyl-5-oxopyrrolidine-2,3,4-triyl triacetate；[(2R,3R,4S)-2,4-diacetyloxy-1-benzyl-5-oxopyrrolidin-3-yl] acetate
• CAS: 155397-98-1
• 化学式: C₁₇H₁₉NO₇
• 分子量: 349.34
• InChiKey: UYUVTJQCTNMFTG-ZMSDIMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酸酐 、 Acetic acid (3R,4S)-4-acetoxy-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成 Acetic acid (2S,3S,4R)-3,4-diacetoxy-1-benzyl-5-oxo-pyrrolidin-2-yl ester 、 (3S,4R,5R)-1-benzyl-3,4,5-triacetoxypyrrolidin-2-one
  参考文献：
  名称：

  Oxazaborolidine catalyzed enantioselective reductions of cyclic meso-imides

  摘要：

  A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 75-89% by both chiral HPLC-determinations and conversion of the reduction products into the corresponding, known lactones.

  DOI：

  10.1016/s0040-4039(00)79972-2

文献信息

• Oxazaborolidine catalyzed enantioselective reductions of cyclic meso-imides
  作者：Romeo Romagnoli、Eric C. Roos、Henk Hiemstra、Marinus J. Moolenaar、W. Nico Speckamp、Bernard Kaptein、Hans E. Schoemaker

  DOI：10.1016/s0040-4039(00)79972-2

  日期：1994.2

  A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 75-89% by both chiral HPLC-determinations and conversion of the reduction products into the corresponding, known lactones.