1,5-anhydro-3,4-O-(cyclohexane-1,1-diyl)-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol | 828268-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-3,4-O-(cyclohexane-1,1-diyl)-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol
• CAS: 828268-88-8
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: NNFNBJNEVSDMNR-GRYCIOLGSA-N

物化性质

• 沸点：
  298.8±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-3,4-O-(cyclohexane-1,1-diyl)-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol 在 palladium on activated charcoal disodium hydrogenphosphate 、 sodium azide 、 disodium hydrogenphosphate 、 氢气 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 504060.0h， 生成 N-(5a-carba-β-L-fucopyranos-1-yl)-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：

  3-O-benzoyl-1,5-anhydro-2,6-dideoxy-4-O-mesyl-5a-carba-DL-arabino-hex-1-enitol 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1,5-anhydro-3,4-O-(cyclohexane-1,1-diyl)-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol
  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