2,3,4,6-tetra-O-benzyl-1-O-(6-bromohexyl)-α-D-glucopyranose | 1334774-37-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3,4,6-tetra-O-benzyl-1-O-(6-bromohexyl)-α-D-glucopyranose
• CAS: 1334774-37-6
• 化学式: C₄₀H₄₇BrO₆
• 分子量: 703.714
• InChiKey: BJXSVWOFEZAHCF-DTQLOPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  47.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,2,6-tri-O-benzyl-N-benzyloxycarbonyl-1-deoxynojirimycin 、 2,3,4,6-tetra-O-benzyl-1-O-(6-bromohexyl)-α-D-glucopyranose 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以61%的产率得到(2R,3R,4R,5S)-4,5-dibenzyloxy-1-benzyloxycarbonyl-2-benzyloxymethyl-3-[6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)hexyloxy]piperidine
  参考文献：
  名称：

  Synthesis and α-amylase inhibitory activity of glucose–deoxynojirimycin conjugates

  摘要：

  Inhibitors of alpha-amylase have attracted attention for their putative effects against diabetes mellitus. Although numerous studies have explored natural small molecule inhibitors, acarbose is currently the only compound with sufficient inhibitory potency and drug-like characteristics to be considered as a potential therapeutic agent. We have synthesized conjugates of the potent glucosidase inhibitor, 1-deoxynojirimycin, and glucose, with the aim of enhancing inhibitory activity against alpha-amylase. This synthetic conjugate showed increased inhibition of alpha-amylase compared to 1-deoxynojirimycin alone, suggesting that similar modifications of existing glucosidase inhibitors may yield more potent alpha-amylase inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.012
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 、 6-溴正己醇 在 四溴化碳 、 三苯基膦 、 四乙基溴化铵 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以100%的产率得到2,3,4,6-tetra-O-benzyl-1-O-(6-bromohexyl)-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis and α-amylase inhibitory activity of glucose–deoxynojirimycin conjugates

  摘要：

  Inhibitors of alpha-amylase have attracted attention for their putative effects against diabetes mellitus. Although numerous studies have explored natural small molecule inhibitors, acarbose is currently the only compound with sufficient inhibitory potency and drug-like characteristics to be considered as a potential therapeutic agent. We have synthesized conjugates of the potent glucosidase inhibitor, 1-deoxynojirimycin, and glucose, with the aim of enhancing inhibitory activity against alpha-amylase. This synthetic conjugate showed increased inhibition of alpha-amylase compared to 1-deoxynojirimycin alone, suggesting that similar modifications of existing glucosidase inhibitors may yield more potent alpha-amylase inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.012