methyl (3R,5S)-2-benzyl-3-[(4'R,5'S)-5'-(hydroxymethyl)-2,2'-dimethyl-1',3'-dioxolan-4'-yl]isoxazolidine-5-carboxylate | 1060657-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3R,5S)-2-benzyl-3-[(4'R,5'S)-5'-(hydroxymethyl)-2,2'-dimethyl-1',3'-dioxolan-4'-yl]isoxazolidine-5-carboxylate
• 英文别名: methyl (3R,5S)-2-benzyl-3-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-oxazolidine-5-carboxylate
• CAS: 1060657-95-5
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: RUXJQHPWPGALRC-FXUDXRNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (3R,5S)-2-benzyl-3-[(4'R,5'S)-5'-(hydroxymethyl)-2,2'-dimethyl-1',3'-dioxolan-4'-yl]isoxazolidine-5-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以92%的产率得到(3S,5R)-3-hydroxy-5-[(4'R,5'S)-5'-(hydroxymethyl)-2,2'-dimethyl-1',3'-dioxolan-4'-yl]-2-pyrrolidone
  参考文献：
  名称：

  A convenient synthesis of new enantiomerically pure trihydroxypyrrolizidines using l-erythrose glycosylhydroxylamine as a masked acyclic chiral nitrone

  摘要：

  A route has been developed for the synthesis of enantiomerically pure trihydroxylated pyrrolizidines starting from L-erythrose glycosylhydroxylamine. The latter acts as a masked acyclic nitrone and reacts diastereoselectively from its Re-face with methyl acrylate to give the corresponding isoxazolidines, which after reductive N-O cleavage are recyclized to trihydroxypyrrolizidines via a Mitsunobu condensation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.093
• 作为产物：
  描述：

  (2S,3S,4S)-N-benzyl-N-hydroxy-3,4-isopropylidenedioxytetrahydrofuran-2-amine 、 丙烯酸甲酯（MA） 反应 48.0h， 以61%的产率得到methyl (3R,5R)-2-benzyl-3-[(4'R,5'S)-5'-(hydroxymethyl)-2,2'-dimethyl-1',3'-dioxolan-4'-yl]isoxazolidine-5-carboxylate
  参考文献：
  名称：

  A convenient synthesis of new enantiomerically pure trihydroxypyrrolizidines using l-erythrose glycosylhydroxylamine as a masked acyclic chiral nitrone

  摘要：

  A route has been developed for the synthesis of enantiomerically pure trihydroxylated pyrrolizidines starting from L-erythrose glycosylhydroxylamine. The latter acts as a masked acyclic nitrone and reacts diastereoselectively from its Re-face with methyl acrylate to give the corresponding isoxazolidines, which after reductive N-O cleavage are recyclized to trihydroxypyrrolizidines via a Mitsunobu condensation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.093