Acetic acid (2R,3R,4R,5S,6R)-5-acetoxy-4-benzyloxy-2-benzyloxymethyl-6-((E)-non-2-enyl)-piperidin-3-yl ester | 819084-39-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Acetic acid (2R,3R,4R,5S,6R)-5-acetoxy-4-benzyloxy-2-benzyloxymethyl-6-((E)-non-2-enyl)-piperidin-3-yl ester
• CAS: 819084-39-4
• 化学式: C₃₃H₄₅NO₆
• 分子量: 551.723
• InChiKey: OXJZDWUNKRTTPZ-ARTPHAODSA-N

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5S,6R)-5-acetoxy-4-benzyloxy-2-benzyloxymethyl-6-((E)-non-2-enyl)-piperidin-3-yl ester 在 palladium on activated charcoal 盐酸 、 甲醇 、 氢气 、 sodium 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 α-1-C-nonyl-1-deoxynojirimycin
  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：

  Acetic acid (2R,3R,4R,5S,6R)-5-acetoxy-6-allyl-4-benzyloxy-2-benzyloxymethyl-1-(2,2,2-trichloro-acetyl)-piperidin-3-yl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 溶剂黄146 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 Acetic acid (2R,3R,4R,5S,6R)-5-acetoxy-4-benzyloxy-2-benzyloxymethyl-6-((E)-non-2-enyl)-piperidin-3-yl ester
  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