methyl (2S,3R,4S)-4-hydroxy-2-[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-oxo-3-pyrrolidinecarboxylate | 1161850-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (2S,3R,4S)-4-hydroxy-2-[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-oxo-3-pyrrolidinecarboxylate
• 英文别名: methyl (2S,3R,4S)-4-hydroxy-2-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-oxopyrrolidine-3-carboxylate
• CAS: 1161850-41-4
• 化学式: C₁₂H₁₉NO₇
• 分子量: 289.285
• InChiKey: JKNGIXDQEFNYFN-XGQMLPDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4S)-4-hydroxy-2-[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-oxo-3-pyrrolidinecarboxylate 、 甲基磺酰氯 在 吡啶 作用下， 反应 2.0h， 以64%的产率得到methyl (2S,3R,4S)-2-[(4'S,5'R)-2',2'-dimethyl-5'-{[(methylsulfonyl)oxy]methyl}-1',3'-dioxolan-4'-yl]-4-hydroxy-5-oxo-3-pyrrolidinecarboxylate
  参考文献：
  名称：

  N-Glycosylhydroxylamines as Masked Polyhydroxylated Chiral Nitrones in Cycloaddition Reactions: An Access to Pyrrolizidines

  摘要：

  N-glycosylhydroxylamines undergo 1,3-dipolar cycloadditions via their tautomeric open chain nitrones. Cycloadditions to maleic acid esters occur with high diastereoselectivity and the products can be converted into highly functionalized pyrrolizidines.

  DOI：

  10.3987/com-08-s(d)59
• 作为产物：
  描述：

  dimethyl (3S,4R,5S)-2-benzyl-3-[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4,5-isoxazolidinedicarboxylate 在 Pd(OH)2/C 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以81%的产率得到methyl (2S,3R,4S)-4-hydroxy-2-[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-oxo-3-pyrrolidinecarboxylate
  参考文献：
  名称：

  N-Glycosylhydroxylamines as Masked Polyhydroxylated Chiral Nitrones in Cycloaddition Reactions: An Access to Pyrrolizidines

  摘要：

  N-glycosylhydroxylamines undergo 1,3-dipolar cycloadditions via their tautomeric open chain nitrones. Cycloadditions to maleic acid esters occur with high diastereoselectivity and the products can be converted into highly functionalized pyrrolizidines.

  DOI：

  10.3987/com-08-s(d)59