(2R,3R,3aR,7aR)-2,3-O-isopropylidene-3a-hydroxy-6-(benzyloxycarbonyl)octahydrofuro[2,3-c]pyridine | 1020066-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,3aR,7aR)-2,3-O-isopropylidene-3a-hydroxy-6-(benzyloxycarbonyl)octahydrofuro[2,3-c]pyridine
• 英文别名: benzyl (1R,2R,6R,8R)-1-hydroxy-4,4-dimethyl-3,5,7-trioxa-10-azatricyclo[6.4.0.02,6]dodecane-10-carboxylate
• CAS: 1020066-62-9
• 化学式: C₁₈H₂₃NO₆
• 分子量: 349.384
• InChiKey: MIJJIBRYQBIMEU-BASYENTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (2R,3R,3aR,7aR)-2,3-O-isopropylidene-3a-hydroxy-6-(benzyloxycarbonyl)octahydrofuro[2,3-c]pyridine 在 三氟乙酸 、 sodium tetrahydroborate 作用下， 以 水 、 四氢呋喃 为溶剂， 反应 3.5h， 以70%的产率得到(3R,4R)-3,4-dihydroxy-4-((S)-1,2-dihydroxyethyl)-N-(benzyloxycarbonyl)piperidine
  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：

  、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 以0.065 g的产率得到(2R,3R,3aR,7aR)-2,3-O-isopropylidene-3a-hydroxy-6-(benzyloxycarbonyl)octahydrofuro[2,3-c]pyridine
  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