5-azidopentyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside | 1169693-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azidopentyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
• CAS: 1169693-77-9
• 化学式: C₃₅H₃₈N₄O₈
• 分子量: 642.709
• InChiKey: BWELYDMPOJDFES-PVEIOGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  47.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  149.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-azidopentyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.17h， 以94%的产率得到5-azidopentyl-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  高效高效制备天然唾液酸苷的高选择性α-唾液酸磷酸酯供体

  摘要：

  哈勃，气泡，辛劳和麻烦：使用新的唾液酸磷酸酯供体可以立体选择性地单锅多组分合成α-唾液寡糖（参见方案）。

  DOI：

  10.1002/chem.200903035
• 作为产物：
  描述：

  (2R,3S,4R,5R,6S)-4-(benzyloxy)-2-((benzyloxy)methyl)-5-(1,3-dioxoisoindolin-2-yl)-6-(p-tolylthio)tetrahydro-2H-pyran-3-yl acetate 、 5-叠氮戊醇,5-AZIDO-1-PENTANOL 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以92%的产率得到5-azidopentyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
  参考文献：
  名称：

  高效高效制备天然唾液酸苷的高选择性α-唾液酸磷酸酯供体

  摘要：

  哈勃，气泡，辛劳和麻烦：使用新的唾液酸磷酸酯供体可以立体选择性地单锅多组分合成α-唾液寡糖（参见方案）。

  DOI：

  10.1002/chem.200903035

文献信息

• Differential Receptor Binding Affinities of Influenza Hemagglutinins on Glycan Arrays
  作者：Hsin-Yu Liao、Che-Hsiung Hsu、Shih-Chi Wang、Chi-Hui Liang、Hsin-Yung Yen、Ching-Yao Su、Chien-Hung Chen、Jia-Tsrong Jan、Chien-Tai Ren、Chung-Hsuan Chen、Ting-Jen R. Cheng、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/ja104657b

  日期：2010.10.27

  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.
• Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates
  作者：Sonia Serna、Bharat Kardak、Niels-Christian Reichardt、Manuel Martin-Lomas

  DOI：10.1016/j.tetasy.2009.02.028

  日期：2009.5

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.