(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-2,6-di-O-acetyl-N-decyl-1,5-dideoxy-1,5-imino-D-glucitol | 418763-63-0

• 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: (4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-2,6-di-O-acetyl-N-decyl-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-2-[(2R,3R,4R,5S)-5-acetyloxy-2-(acetyloxymethyl)-1-decyl-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxypiperidin-3-yl]oxy-6-(acetyloxymethyl)-4-hydroxyoxan-3-yl] benzoate
• CAS: 418763-63-0
• 化学式: C₄₉H₇₁NO₂₁
• 分子量: 1010.1
• InChiKey: CUVMOYBNJWBQAU-IPTMJJFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  71
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  271
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-2,6-di-O-acetyl-N-decyl-1,5-dideoxy-1,5-imino-D-glucitol 在 pyridine-SO3 complex 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以88%的产率得到(4,6-di-O-acetyl-2-O-benzoyl-3-O-sulfo-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-2,6-di-O-acetyl-N-decyl-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：

  (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-decyl-1,5-dideoxy-1,5-imino-D-glucitol 在 乙酸肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以95%的产率得到(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-2,6-di-O-acetyl-N-decyl-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