(2-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-[(α-L-fucopyranosyl)-(1->3)]-2-O-acetyl-N-butyl-1,5-dideoxy-1,5-imino-D-glucitol | 418763-57-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-[(α-L-fucopyranosyl)-(1->3)]-2-O-acetyl-N-butyl-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: [(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-5-acetyloxy-1-butyl-2-(hydroxymethyl)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypiperidin-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(4-oxopentanoyloxy)oxan-3-yl] benzoate
• CAS: 418763-57-2
• 化学式: C₃₆H₅₃NO₁₇
• 分子量: 771.813
• InChiKey: KDIVMVLXBMZFJU-RRPRBDBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  258
• 氢给体数：
  6
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-[(α-L-fucopyranosyl)-(1->3)]-2-O-acetyl-N-butyl-1,5-dideoxy-1,5-imino-D-glucitol 在 吡啶 作用下， 以60 mg的产率得到(4,6-di-O-acetyl-2-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-2,6-di-O-acetyl-N-butyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  SYNTHESIS OF SIALYL- AND SULFO-Le^x/Le^aANALOGS CONTAININGN-ALKYL-1-DEOXYNOJIRIMYCIN AS POTENTIAL SELECTIN BLOCKERS

  摘要：

  A series of novel sialyl- and sulfo-Le(x)/Le(a) oligosaccharides containing N-alkyl-1-deoxynojirimycin as potential selectin blockers have systematically been synthesized via the suitably protected intermediates containing N-benzyloxycarbonyl-1-deoxynojirimycin. Some of the synthetic oligosaccharides strongly inhibited the adhesion of HL60 cells to IL-1beta-stimulated HUVECs.

  DOI：

  10.1081/car-100108657
• 作为产物：
  描述：

  methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-β-D-galactopyranoside 在 palladium dihydroxide 、 钯 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 正丁醇 为溶剂， 生成 (2-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-[(α-L-fucopyranosyl)-(1->3)]-2-O-acetyl-N-butyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  SYNTHESIS OF SIALYL- AND SULFO-Le^x/Le^aANALOGS CONTAININGN-ALKYL-1-DEOXYNOJIRIMYCIN AS POTENTIAL SELECTIN BLOCKERS

  摘要：

  A series of novel sialyl- and sulfo-Le(x)/Le(a) oligosaccharides containing N-alkyl-1-deoxynojirimycin as potential selectin blockers have systematically been synthesized via the suitably protected intermediates containing N-benzyloxycarbonyl-1-deoxynojirimycin. Some of the synthetic oligosaccharides strongly inhibited the adhesion of HL60 cells to IL-1beta-stimulated HUVECs.

  DOI：

  10.1081/car-100108657