6-O-[6-O-(2-trifluoroacetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide | 1429306-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-[6-O-(2-trifluoroacetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-6-azido-3,4-dibenzoyloxy-5-(1-hydroxyethylideneamino)oxan-2-yl]methoxy]-4,5-dibenzoyloxy-6-[[(2R,3R,4R,5S,6R)-4,5-dibenzoyloxy-6-(benzoyloxymethyl)-3-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl]oxymethyl]oxan-3-yl]-2,2,2-trifluoroethanimidic acid
• CAS: 1429306-59-1
• 化学式: C₇₃H₆₂F₆N₆O₂₂
• 分子量: 1489.31
• InChiKey: BYWHKWVIIFIBPB-ZAQSKFIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  107
• 可旋转键数：
  32
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  342
• 氢给体数：
  3
• 氢受体数：
  33

反应信息

• 作为产物：
  描述：

  ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside 、 6-O-(2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 以95%的产率得到6-O-[6-O-(2-trifluoroacetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides

  摘要：

  Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the method with the formation of a pentasaccharide. The key building block is an orthogonally protected N-trifluoroacetamido thioglycoside donor that was added in succession to a glycosyl acceptor, enabling efficient glycosylation of the growing chain. In the second step of the iterative cycle, this building block is quantitatively deprotected at the C-6-hydroxyl position, ready for the next saccharide addition. Building from an azido-functionalised GlcNAc monosaccharide acceptor, the pentasaccharide was synthesised in seven steps in an overall yield of 25%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.01.008

文献信息

• A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides
  作者：Lucy G. Weaver、Yogendra Singh、Joanne T. Blanchfield、Paul L. Burn

  DOI：10.1016/j.carres.2013.01.008

  日期：2013.4

  Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the method with the formation of a pentasaccharide. The key building block is an orthogonally protected N-trifluoroacetamido thioglycoside donor that was added in succession to a glycosyl acceptor, enabling efficient glycosylation of the growing chain. In the second step of the iterative cycle, this building block is quantitatively deprotected at the C-6-hydroxyl position, ready for the next saccharide addition. Building from an azido-functionalised GlcNAc monosaccharide acceptor, the pentasaccharide was synthesised in seven steps in an overall yield of 25%. (C) 2013 Elsevier Ltd. All rights reserved.