3-acetamidopropyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranoside | 1308292-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetamidopropyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranoside
• CAS: 1308292-93-4
• 化学式: C₆₃H₁₁₄N₁₀O₄₀
• 分子量: 1651.64
• InChiKey: OLPBXNFELNJEFC-MTWIXXLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -20.02
• 重原子数：
  113.0
• 可旋转键数：
  32.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  819.95
• 氢给体数：
  29.0
• 氢受体数：
  47.0

反应信息

• 作为产物：
  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 、 、 乙酰氯 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 以12 mg的产率得到3-acetamidopropyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-β-D-glucopyranosyl-(1-> 6)-2-amino-2-deoxy-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