2,3-di-O-acetyl-N-benzyloxycarbonyl-4,6-di-O-(p-tolylsulfonyl)-5a-carba-D-glucopyranosylamine | 191723-81-6

• 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: 2,3-di-O-acetyl-N-benzyloxycarbonyl-4,6-di-O-(p-tolylsulfonyl)-5a-carba-D-glucopyranosylamine
• CAS: 191723-81-6
• 化学式: C₃₃H₃₇NO₁₂S₂
• 分子量: 703.788
• InChiKey: SSGWEEXWRPXEQT-HQNPHDNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  177.67
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-acetyl-N-benzyloxycarbonyl-4,6-di-O-(p-tolylsulfonyl)-5a-carba-D-glucopyranosylamine 在 sodium benzoate 、 barium dihydroxide 作用下， 生成 6-氨基-4-(羟甲基)-4-环己基-[4H,5H]-1,2,3-三醇 、 4-epi-validamine
  参考文献：
  名称：

  Preparation and biological activity of manno- and galacto-validamines, new 5a-carba-glycosylamines as α-glycosidase inhibitors

  摘要：

  Manno- and galacto-validamines, which are epimers of validamine, were semi-synthesized by the configurational inversion of validamine, a pseudo-sugar analogue of alpha-D-glucopyranose that has inhibitory activity for alpha-glucosidases. The inhibitory activities of these analogues were determined against several mannosidases and galactosidases. Manno-validamine shows potent inhibition for the alpha-mannosidases (competitive, K-i = 4.6 x 10(-5) M for jack beans, and competitive, K-i = 2.8 x 10(-5) M for almonds), and galacto-validamine shows weak inhibition for the alpha-galactosidases (coffee bean and E. coli). The inhibitory effect of the epimers on the N-linked oligosaccharide-processing mannosidases involved in glycoprotein biosynthesis and lysosomal mannosidase from rat liver were also examined. Mannovalidamine shows potent inhibition on the endoplasmic reticulumal alpha-mannosidase (competitive, K-i = 1.2 x 10(-6) M), Golgi mannosidases IA, II (competitive, K-i = 2.8 x 10(-5) M), and lysosomal alpha-mannosidase (competitive, K-i = 1.7 x 10(-5) M). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00052-9
• 作为产物：
  描述：

  4,6-O-benzylidene-N-benzyloxycarbonyl-5a-carba-D-glucopyranosylamine 在 盐酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 2,3-di-O-acetyl-N-benzyloxycarbonyl-4,6-di-O-(p-tolylsulfonyl)-5a-carba-D-glucopyranosylamine
  参考文献：
  名称：

  Preparation and biological activity of manno- and galacto-validamines, new 5a-carba-glycosylamines as α-glycosidase inhibitors

  摘要：

  Manno- and galacto-validamines, which are epimers of validamine, were semi-synthesized by the configurational inversion of validamine, a pseudo-sugar analogue of alpha-D-glucopyranose that has inhibitory activity for alpha-glucosidases. The inhibitory activities of these analogues were determined against several mannosidases and galactosidases. Manno-validamine shows potent inhibition for the alpha-mannosidases (competitive, K-i = 4.6 x 10(-5) M for jack beans, and competitive, K-i = 2.8 x 10(-5) M for almonds), and galacto-validamine shows weak inhibition for the alpha-galactosidases (coffee bean and E. coli). The inhibitory effect of the epimers on the N-linked oligosaccharide-processing mannosidases involved in glycoprotein biosynthesis and lysosomal mannosidase from rat liver were also examined. Mannovalidamine shows potent inhibition on the endoplasmic reticulumal alpha-mannosidase (competitive, K-i = 1.2 x 10(-6) M), Golgi mannosidases IA, II (competitive, K-i = 2.8 x 10(-5) M), and lysosomal alpha-mannosidase (competitive, K-i = 1.7 x 10(-5) M). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00052-9