N-dodecyl-6-O-benzyl-3,4-O-isopropylidene-5a-carba-β-D-galactopyranosylamine | 828269-04-1

• 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: N-dodecyl-6-O-benzyl-3,4-O-isopropylidene-5a-carba-β-D-galactopyranosylamine
• CAS: 828269-04-1
• 化学式: C₂₉H₄₉NO₄
• 分子量: 475.712
• InChiKey: WANDDDJNRNUKEH-URYJJRPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  34.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  59.95
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-dodecyl-6-O-benzyl-3,4-O-isopropylidene-5a-carba-β-D-galactopyranosylamine 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 19.0h， 生成 N-dodecyl-5a-carba-β-D-galactopyranosylamine
  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：

  十二烷基伯胺 、 1,2-anhydro-6-O-benzyl-3,4-O-isopropylidene-5a-carba-α-D-galactopyranose 以 异丙醇 为溶剂， 反应 48.0h， 以74%的产率得到N-dodecyl-6-O-benzyl-3,4-O-isopropylidene-5a-carba-β-D-galactopyranosylamine
  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