5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 190269-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 190269-49-9
• 化学式: C₅₆H₆₂N₄O₁₂
• 分子量: 983.128
• InChiKey: GPIUBQNOLBGZSE-LHVGBORSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.11
• 重原子数：
  72.0
• 可旋转键数：
  24.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  178.44
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 乙醇 、 乙二胺 作用下， 反应 16.0h， 生成
  参考文献：
  名称：

  Differential Receptor Binding Affinities of Influenza Hemagglutinins on Glycan Arrays

  摘要：

  A library of 27 sialosides, including seventeen 2,3-linked and ten 2,6-linked glycans, has been prepared to construct a glycan array and used to profile the binding specificity of different influenza hemagglutinins (HA) subtypes, especially from the 2009 swine-originated H1N1 and seasonal influenza viruses. It was found that the HAs from the 2009 H1N1 and the seasonal Brisbane strain share similar binding profiles yet different binding affinities toward various alpha 2,6 sialosides. Analysis of the binding profiles of different HA subtypes indicate that a minimum set of 5 oligosaccharides can be used to differentiate influenza H1, H3, H5, H7, and H9 subtypes. In addition, the glycan array was used to profile the binding pattern of different influenza viruses. It was found that most binding patterns of viruses and HA proteins are similar and that glycosylation at Asn27 is essential for receptor binding.

  DOI：

  10.1021/ja104657b
• 作为产物：
  描述：

  ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopryanoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 sodium methylate 、 对甲苯磺酸 、 三氟乙酸 、 potassium iodide 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the Sda determinant and two analogous tetrasaccharides

  摘要：

  To contribute to the possibility of studying in greater detail the biological significance of Sd(a)-containing glycans as occur in Tamm-Horsfall glycoprotein, the following three spacer-linked tetrasaccharides have been synthesized: the Sd(a) determinant alpha-Neup5Ac-(2 --> 3)-[beta D-GalpNAc-(1 --> 4)]-beta-D-Galp-(1 --> 4)-beta-D-GlcpNAc-(1 --> 0)(CH2)(5)NH2 (1), the Gal-analogue alpha-Neup5Ac-(2 --> 3)-[beta-D-Galp-(1 --> 4)]-beta-D-Galp-(1 --> 4)-beta-D-GlcpNAc-(1 --> 0)(CH2)(5)NH2 (2), and the GlcNAc-analogue alpha-Neup5Ac-(2 --> 3)-[beta-D-GlcpNAc-(1 --> 4)]-beta-D-Galp-(1 --> 4)-beta-D-GlcpNAc-(1 --> 0)(CH2)(5)NH2 (3). The general trisaccharide acceptor 5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonate)-(2 --> 3)-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside was prepared, using methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-non-2-ulopyranosid)-onate as the sialyl donor. For the syntheses of 1, 2, and 3 the glycosyl donors 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-alpha-D-galactopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate, respectively, proved to be the most suitable. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00013-x