(1R,5S,6R,7r,8S)-9-benzyl-6,7,8-tris(benzyloxy)-3-oxa-9-azabicyclo[3.3.1]nonane | 1353483-65-4

• 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: (1R,5S,6R,7r,8S)-9-benzyl-6,7,8-tris(benzyloxy)-3-oxa-9-azabicyclo[3.3.1]nonane
• CAS: 1353483-65-4
• 化学式: C₃₅H₃₇NO₄
• 分子量: 535.683
• InChiKey: WYEFZUDJPKDNAR-AXXIZJNBSA-N

反应信息

• 作为反应物：
  描述：

  (1R,5S,6R,7r,8S)-9-benzyl-6,7,8-tris(benzyloxy)-3-oxa-9-azabicyclo[3.3.1]nonane 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以100%的产率得到(1R,5S,6R,7r,8S)-3-oxa-9-azabicyclo[3.3.1]nonane-6,7,8-triol hydrochloride
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors of Two Ether-Bridged Iminosugars

  摘要：

  Two bicyclic iminosugars have been synthesized from polyhydroxylated azepanes by ring isomerization followed by debenzylative cyclization. Their conformations have been studied by NMR and molecular modeling and their glycosidase inhibition profiles were determined. They both adopt a chair conformation for the piperidine ring and display weak inhibition on alpha-glucosidases.

  DOI：

  10.1080/07328303.2011.630547
• 作为产物：
  描述：

  (2S,3R,4S,5S,6S)-1-benzyl-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(chloromethyl)piperidine 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以64%的产率得到(1R,5S,6R,7r,8S)-9-benzyl-6,7,8-tris(benzyloxy)-3-oxa-9-azabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors of Two Ether-Bridged Iminosugars

  摘要：

  Two bicyclic iminosugars have been synthesized from polyhydroxylated azepanes by ring isomerization followed by debenzylative cyclization. Their conformations have been studied by NMR and molecular modeling and their glycosidase inhibition profiles were determined. They both adopt a chair conformation for the piperidine ring and display weak inhibition on alpha-glucosidases.

  DOI：

  10.1080/07328303.2011.630547