(1S,3R,4R,5R,8R)-2-benzyl-4,8-bis(benzyloxy)-3-(benzyloxymethyl)-6-oxa-2-azabicyclo[3.2.1]octane | 1353483-71-2

• 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: (1S,3R,4R,5R,8R)-2-benzyl-4,8-bis(benzyloxy)-3-(benzyloxymethyl)-6-oxa-2-azabicyclo[3.2.1]octane
• CAS: 1353483-71-2
• 化学式: C₃₅H₃₇NO₄
• 分子量: 535.683
• InChiKey: NLRLQGZEJBCJPO-LJVKMUTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5R,8R)-2-benzyl-4,8-bis(benzyloxy)-3-(benzyloxymethyl)-6-oxa-2-azabicyclo[3.2.1]octane 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70%的产率得到(1S,3R,4R,5S,8R)-3-(hydroxymethyl)-6-oxa-2-azabicyclo[3.2.1]octane-4,8-diol 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：

  (2R,3R,4S,5R,6R)-1-benzyl-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)azepan-6-ol 在 甲基磺酰氯 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (1S,3R,4R,5R,8R)-2-benzyl-4,8-bis(benzyloxy)-3-(benzyloxymethyl)-6-oxa-2-azabicyclo[3.2.1]octane
  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