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 | 1161850-42-5

• 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)-2-[(4'S,5'R)-2',2'-dimethyl-5'-{[(methylsulfonyl)oxy]methyl}-1',3'-dioxolan-4'-yl]-4-hydroxy-5-oxo-3-pyrrolidinecarboxylate
• 英文别名: methyl (2S,3R,4S)-2-[(4S,5R)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-1,3-dioxolan-4-yl]-4-hydroxy-5-oxopyrrolidine-3-carboxylate
• CAS: 1161850-42-5
• 化学式: C₁₃H₂₁NO₉S
• 分子量: 367.377
• InChiKey: IMIQMRUHALTYFL-FHNUBNKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  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 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 以30%的产率得到methyl (3aR,7S,8R,8aS,8bS)-7-hydroxy-2,2-dimethyl-6-oxohexahydro-4H-[1,3]-dioxolo[4,5-a]pyrrolizine-8-carboxylate
  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：

  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