Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine | 819084-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine
• CAS: 819084-35-0
• 化学式: C₃₆H₄₇NO₅
• 分子量: 573.773
• InChiKey: VBGIUKRKENTEQC-IOOWNVKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.18
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine 在 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 (2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-hexyl-piperidine-3,5-diol
  参考文献：
  名称：

  α-1-C-Alkyl-1-deoxynojirimycin derivatives as potent and selective inhibitors of intestinal isomaltase: remarkable effect of the alkyl chain length on glycosidase inhibitory profile

  摘要：

  A series of alpha- and beta-1-C-alkyl-1-deoxynojirimycin derivatives was prepared and evaluated as glycosidase inhibitors. Biological assays showed a marked dependence of the selectivity and potency of the inhibitors upon the position of the alkyl chain (alpha-1-C-, beta-1-C- or N-alkyl derivatives). In addition, the efficiency of alpha-1-C-alkyl-1-deoxynojirimycin derivatives as intestinal isomaltase inhibitors increases with the length of the alkyl chain. The strongest inhibition was found for alpha-1-C-nonyl-1-deoxynojirimycin with an IC50 = 3.5 nM (25x more potent inhibitor than the shorter chain homologue carrying a C-8 chain). These results demonstrate that subtle changes in the aglycon fragment may result in remarkable enzyme specificity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.086
• 作为产物：
  描述：

  己基溴化镁 、 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine 以 乙醚 为溶剂， 反应 24.0h， 以59%的产率得到Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine
  参考文献：
  名称：

  α-1-C-Alkyl-1-deoxynojirimycin derivatives as potent and selective inhibitors of intestinal isomaltase: remarkable effect of the alkyl chain length on glycosidase inhibitory profile

  摘要：

  A series of alpha- and beta-1-C-alkyl-1-deoxynojirimycin derivatives was prepared and evaluated as glycosidase inhibitors. Biological assays showed a marked dependence of the selectivity and potency of the inhibitors upon the position of the alkyl chain (alpha-1-C-, beta-1-C- or N-alkyl derivatives). In addition, the efficiency of alpha-1-C-alkyl-1-deoxynojirimycin derivatives as intestinal isomaltase inhibitors increases with the length of the alkyl chain. The strongest inhibition was found for alpha-1-C-nonyl-1-deoxynojirimycin with an IC50 = 3.5 nM (25x more potent inhibitor than the shorter chain homologue carrying a C-8 chain). These results demonstrate that subtle changes in the aglycon fragment may result in remarkable enzyme specificity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.086