1,2-O-isopropylidene-3-C-(1'-(N-benzyl-N-benzyloxycarbonyl)aminoethyl)-α-D-allo-1,4-furanose | 1020066-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-C-(1'-(N-benzyl-N-benzyloxycarbonyl)aminoethyl)-α-D-allo-1,4-furanose
• CAS: 1020066-59-4
• 化学式: C₂₆H₃₃NO₈
• 分子量: 487.55
• InChiKey: PUVNOORATFIKLE-MYIDKPJBSA-N

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-C-(1'-(N-benzyl-N-benzyloxycarbonyl)aminoethyl)-α-D-allo-1,4-furanose 在 sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以89%的产率得到1,2-O-isopropylidene-3-C-(1'-(N-benzyl-N-benzyloxycarbonyl)aminoethyl)-α-D-ribo-pentodialdo-1,4-furanose
  参考文献：
  名称：

  Synthesis of γ-Hydroxyalkyl Substituted Piperidine Iminosugars from d-Glucose

  摘要：

  D-Glucose was converted to synthetic equivalent of meso-pentodialdose, namely 3-C-(1'-aminoethyl)-alpha-D-ribo-pento-dialdo-1,4-furanose 10 that gives an easy access to manipulate the aldehyde functionalities on either sides to get enantiomeric pair of 3. Thus, reduction of C5-aldehyde followed by hydrolysis of 1,2-acetonide functionality and reductive aminocyclization with C1-aldehyde afforded gamma-1,2-dihydroxyethyl piperidine iminosugar 3. On the other hand, first reductive aminocyclization with C5-aldehyde gave piperidine ring skeleton 12 that on removal of 1,2-acetonide and reduction of C1-aldehyde gave ent-3 while chopping of C1-aldehyde in 12 and reduction afforded gamma-hydroxymethyl piperidine immosugar 4.

  DOI：

  10.1021/jo800044r
• 作为产物：
  描述：

  1,2;5,6-di-O-isopropylidene-3-C-(1'-(N-benzyl-N-benzyloxycarbonyl)aminoethyl)-α-D-allo-1,4-furanose 在 高氯酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以86%的产率得到1,2-O-isopropylidene-3-C-(1'-(N-benzyl-N-benzyloxycarbonyl)aminoethyl)-α-D-allo-1,4-furanose
  参考文献：
  名称：

  Synthesis of γ-Hydroxyalkyl Substituted Piperidine Iminosugars from d-Glucose

  摘要：

  D-Glucose was converted to synthetic equivalent of meso-pentodialdose, namely 3-C-(1'-aminoethyl)-alpha-D-ribo-pento-dialdo-1,4-furanose 10 that gives an easy access to manipulate the aldehyde functionalities on either sides to get enantiomeric pair of 3. Thus, reduction of C5-aldehyde followed by hydrolysis of 1,2-acetonide functionality and reductive aminocyclization with C1-aldehyde afforded gamma-1,2-dihydroxyethyl piperidine iminosugar 3. On the other hand, first reductive aminocyclization with C5-aldehyde gave piperidine ring skeleton 12 that on removal of 1,2-acetonide and reduction of C1-aldehyde gave ent-3 while chopping of C1-aldehyde in 12 and reduction afforded gamma-hydroxymethyl piperidine immosugar 4.

  DOI：

  10.1021/jo800044r