(2,4,6-tri-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol | 173273-89-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (2,4,6-tri-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: benzyl (2R,3R,4S,5S)-5-acetyloxy-4-[(2S,3R,4S,5S,6R)-3,5-dibenzoyloxy-6-(benzoyloxymethyl)-4-(4-oxopentanoyloxy)oxan-2-yl]oxy-3-hydroxy-2-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 173273-89-7
• 化学式: C₄₈H₄₉NO₁₇
• 分子量: 911.914
• InChiKey: BOBKLFOGPMFWBH-ISQAKQRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  237
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (2,4,6-tri-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(2,4,6-tri-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-N-benzyloxycarbonyl-6-O-tert-butyldimethylsilyl-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：

  乙酰丙酸酐 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.33h， 生成 (2,4,6-tri-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-N-benzyloxycarbonyl-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