3,4-O-(cyclohexane-1,1-diyl)-5a-carba-β-L-fucopyranosyl azide | 828269-09-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-(cyclohexane-1,1-diyl)-5a-carba-β-L-fucopyranosyl azide
• CAS: 828269-09-6
• 化学式: C₁₃H₂₁N₃O₃
• 分子量: 267.328
• InChiKey: MJVBXFFRGNTHME-ROHXPCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,4-O-(cyclohexane-1,1-diyl)-5a-carba-β-L-fucopyranosyl azide 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 5a-carba-β-L-fucopyranosylamine
  参考文献：
  名称：

  Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives

  摘要：

  In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-(D)-galactopyranosylamitie demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-(D)-galactopyranosylatnines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.023
• 作为产物：
  描述：

  1,5-anhydro-3,4-O-(cyclohexane-1,1-diyl)-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol 在 disodium hydrogenphosphate 、 sodium azide 、 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 3,4-O-(cyclohexane-1,1-diyl)-5a-carba-β-L-fucopyranosyl azide
  参考文献：
  名称：

  Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives

  摘要：

  In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-(D)-galactopyranosylamitie demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-(D)-galactopyranosylatnines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.023