4-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose | 649571-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose
• 英文别名: (3R,5S)-5-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-1-benzyl-3-hydroxypyrrolidin-2-one
• CAS: 649571-90-4
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: PAWXFNLUPYTZEB-BLVXYGRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 4-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以97%的产率得到4-{(3R,5S)-1-benzyl-3-[(1R)-1-methoxy-1-phenyl-1-(trifluoromethyl)acetoxy]-2-oxo-5-pyrrolidinyl}-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027
• 作为产物：
  描述：

  (Z)-N-(5-deoxy-2,3-0-isopropylidene-l-O-methyl-D-yxo-l,4-furanose-5-ylidene)benzylamine N-oxide 在 水 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 4-[(3R,5S)-1-benzyl-3-hydroxy-2-oxo-5-pyrrolidinyl]-2,3-O-isopropylidene-1-O-methyl-α-D-lyxo-tetrofuranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027