ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside | 1429306-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside
• CAS: 1429306-54-6
• 化学式: C₃₁H₂₈F₃NO₈S
• 分子量: 631.626
• InChiKey: HEKANZKLXAUZGQ-LPSUVQJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  ethyl 2-trifluoroacetamido-3,4,6-tri-O-acetyl-1-thio-2-deoxy-β-D-glucopyranoside 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside
  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