ethyl 6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 6)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl-(1-> 6)-3,4-di-O-benzoyl-2-deoxy-1-thio-2-phthalimido-β-D-glucopyranoside | 1308292-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 6)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl-(1-> 6)-3,4-di-O-benzoyl-2-deoxy-1-thio-2-phthalimido-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-6-(acetyloxymethyl)-4,5-dibenzoyloxy-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxymethyl]-4,5-dibenzoyloxy-2-[[(2R,3S,4R,5R,6S)-3,4-dibenzoyloxy-5-(1,3-dioxoisoindol-2-yl)-6-ethylsulfanyloxan-2-yl]methoxy]oxan-3-yl]ethanimidic acid
• CAS: 1308292-85-4
• 化学式: C₈₂H₇₁N₃O₂₄S
• 分子量: 1514.54
• InChiKey: TYDMMYGGGUIEBN-OZJLSDTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  110
• 可旋转键数：
  32
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  363
• 氢给体数：
  1
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 6)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl-(1-> 6)-3,4-di-O-benzoyl-2-deoxy-1-thio-2-phthalimido-β-D-glucopyranoside 、 3-(苄氧羰基氨基)-1-丙醇 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of five nona-β-(1→6)-d-glucosamines with various patterns of N-acetylation corresponding to the fragments of exopolysaccharide of Staphylococcus aureus

  摘要：

  A series of five 3-acetamidopropyl beta-glycosides of nona-beta-(1 -> 6)-glucosamines containing two N-acetyl-glucosamine residues separated by a different number of glucosamine units with free amino groups have been synthesized using a convergent blockwise approach. Oxazoline glycosylation was used to introduce N-acetylglucosamine residues. These nonasaccharides are structurally related to the poly-N-acetylglucosamine (PNAG) extracellular polysaccharide of Staphylococcus aureus and can be used as models for biochemical and immunological studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.018
• 作为产物：
  描述：

  [(2R,3S,4R,5R,6S)-2-(acetyloxymethyl)-4-benzoyloxy-6-bromo-5-(1,3-dioxoisoindol-2-yl)oxan-3-yl] benzoate 、 在 mercury(II) cyanide 、 mercury dibromide 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以91%的产率得到ethyl 6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 6)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl-(1-> 6)-3,4-di-O-benzoyl-2-deoxy-1-thio-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of five nona-β-(1→6)-d-glucosamines with various patterns of N-acetylation corresponding to the fragments of exopolysaccharide of Staphylococcus aureus

  摘要：

  A series of five 3-acetamidopropyl beta-glycosides of nona-beta-(1 -> 6)-glucosamines containing two N-acetyl-glucosamine residues separated by a different number of glucosamine units with free amino groups have been synthesized using a convergent blockwise approach. Oxazoline glycosylation was used to introduce N-acetylglucosamine residues. These nonasaccharides are structurally related to the poly-N-acetylglucosamine (PNAG) extracellular polysaccharide of Staphylococcus aureus and can be used as models for biochemical and immunological studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.018