dimethyl (3S,4R,5S)-2-benzyl-3-{(R)-hydroxy[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]methyl}-4,5-isoxazolidinedicarboxylate | 1161850-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl (3S,4R,5S)-2-benzyl-3-{(R)-hydroxy[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]methyl}-4,5-isoxazolidinedicarboxylate
• 英文别名: dimethyl (3S,4R,5S)-2-benzyl-3-[(R)-hydroxy-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-1,2-oxazolidine-4,5-dicarboxylate
• CAS: 1161850-39-0
• 化学式: C₂₁H₂₉NO₉
• 分子量: 439.463
• InChiKey: IGDPXDGUMOQSGH-PNVOZDDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  马来酸二甲酯 、 (3aR,7S,7aS)-6-(Benzyl-hydroxy-amino)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 反应 12.0h， 生成 dimethyl (3R,4S,5R)-2-benzyl-3-{(R)-hydroxy[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]methyl}-4,5-isoxazolidinedicarboxylate 、 dimethyl (3S,4R,5S)-2-benzyl-3-{(R)-hydroxy[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]methyl}-4,5-isoxazolidinedicarboxylate
  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