(2S,3R,4R)-1-(4-sulphonamidophenethyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)piperidine | 1600532-70-4

• 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: (2S,3R,4R)-1-(4-sulphonamidophenethyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)piperidine
• CAS: 1600532-70-4
• 化学式: C₃₅H₄₀N₂O₅S
• 分子量: 600.779
• InChiKey: VQKFTMQEWSZOJV-BMPTZRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  91.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-1-(4-sulphonamidophenethyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)piperidine 在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 48.0h， 以60%的产率得到(2S,3R,4R)-1-(4-sulphonamidophenethyl)-2-(hydroxymethyl)piperidine-3,4-diol
  参考文献：
  名称：

  A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition

  摘要：

  A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselective reaction (de value > 98%). It is disclosed that bulky substituent at N atom of the piperidine decreases the inhibition activity except those substituents having the ability of salvation or forming disulfide bond with M444 at the active site of alpha-glycosidase, which enhance the interaction with enzyme. Compounds with S-configuration at C-3 show greater activity than those with R-configuration. The structure activity relationship study is also supported by molecular docking analysis. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.004
• 作为产物：
  描述：

  (3R,4R,5R)-3,4,6-tris(benzyloxy)hexane-1,5-diol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 (2S,3R,4R)-1-(4-sulphonamidophenethyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)piperidine
  参考文献：
  名称：

  A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition

  摘要：

  A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselective reaction (de value > 98%). It is disclosed that bulky substituent at N atom of the piperidine decreases the inhibition activity except those substituents having the ability of salvation or forming disulfide bond with M444 at the active site of alpha-glycosidase, which enhance the interaction with enzyme. Compounds with S-configuration at C-3 show greater activity than those with R-configuration. The structure activity relationship study is also supported by molecular docking analysis. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.004