(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-(β-D-galactopyranosyl)-(1->4)-[α-L-fucopyranosyl-(1->3)]-1,5-dideoxy-1,5-imino-D-glucitol | 143572-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-(β-D-galactopyranosyl)-(1->4)-[α-L-fucopyranosyl-(1->3)]-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: (2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-2-[(2R,3R,4R,5S)-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypiperidin-3-yl]oxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 143572-03-6
• 化学式: C₂₉H₅₀N₂O₂₁
• 分子量: 762.717
• InChiKey: HDIXPZDLRNMSBI-PCGQOHRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.3
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  377
• 氢给体数：
  15
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-O-acetyl-1,5-dideoxy-1,5-imino-D-glucitol 在 sodium methylate 、 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 以17.8 mg的产率得到(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-(β-D-galactopyranosyl)-(1->4)-[α-L-fucopyranosyl-(1->3)]-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

文献信息

• Synthesis of 1-deoxynojirimycin-containing glycans related to the Lewis X and sialyl-Lewis X epitopes recognized by LEC-CAMs
  作者：Hiroyasu Furui、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/s0008-6215(00)90493-2

  日期：1992.5
• SYNTHESIS OF SIALYL- AND SULFO-Le^x/Le^aANALOGS CONTAINING<i>N</i>-ALKYL-1-DEOXYNOJIRIMYCIN AS POTENTIAL SELECTIN BLOCKERS
  作者：Hiroyasu Furui[2]、Keiko Ando-Furui、Haruko Inagaki、Takayuki Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1081/car-100108657

  日期：2001.12.31

  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.