6-O-[6-O-(2-trifluoroacetamido-3,4-di-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 | 1429306-61-5

• 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-di-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: TfaNH(-2d)[Bz(-3)][Bz(-4)]Glc(b1-6)[TfaNH(-2d)][Bz(-3)][Bz(-4)]Glc(b1-6)[Bz(-3)][Bz(-4)]GlcNAc(b)-N3；[(2R,3S,4R,5R,6R)-6-[[(2R,3S,4R,5R,6R)-6-[[(2R,3S,4R,5R,6R)-5-acetamido-6-azido-3,4-dibenzoyloxyoxan-2-yl]methoxy]-3,4-dibenzoyloxy-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]methoxy]-4-benzoyloxy-2-(hydroxymethyl)-5-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] benzoate
• CAS: 1429306-61-5
• 化学式: C₆₆H₅₈F₆N₆O₂₁
• 分子量: 1385.2
• InChiKey: IZANBEONGNBKEX-YHENTUGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  99
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  326
• 氢给体数：
  4
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  6-O-[6-O-(2-trifluoroacetamido-3,4-di-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 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 23.5h， 以70%的产率得到6-O-[6-O-(6-O-[2-trifluoroacetamido-6-O-tert-butyldiphenylsilyl-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-trifluoroacetamido-3,4-di-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
• 作为产物：
  描述：

  6-O-[6-O-(2-trifluoroacetamido-6-O-tert-butyldiphenylsilyl 3,4-di-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 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以100%的产率得到6-O-[6-O-(2-trifluoroacetamido-3,4-di-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