2-methyl-(6-O-acetyl-3,4-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline | 1308292-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-(6-O-acetyl-3,4-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline
• 英文别名: [(3aR,5R,6S,7R,7aR)-5-(acetyloxymethyl)-7-benzoyloxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-6-yl] benzoate
• CAS: 1308292-81-0
• 化学式: C₂₄H₂₃NO₈
• 分子量: 453.449
• InChiKey: OHYAOTUDAJCQDM-NQZVWWGESA-N

物化性质

• 沸点：
  579.4±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-methyl-(6-O-acetyl-3,4-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline 在 甲醇 、 三氟甲磺酸 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 56.0h， 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)-5-acetamido-4,6-dibenzoyloxy-2-(trityloxymethyl)oxan-3-yl] benzoate 在 iron(III) chloride 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-methyl-(6-O-acetyl-3,4-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline
  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