2-acetamido-2-deoxy-4-phospho-D-glucopyranose | 73458-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-4-phospho-D-glucopyranose
• 英文别名: 2-acetamido-2-deoxy-4-O-phosphono-beta-D-glucopyranose；[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl] dihydrogen phosphate
• CAS: 73458-53-4
• 化学式: C₈H₁₆NO₉P
• 分子量: 301.19
• InChiKey: DHZPCJWLUQMUPF-FMDGEEDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside 在 四氮唑 、 palladium 10% on activated carbon 、 氢气 、 乙二胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.17h， 生成 2-acetamido-2-deoxy-4-phospho-D-glucopyranose 、 2-acetamido-2-deoxy-4-phospho-D-glucopyranose
  参考文献：
  名称：

  Efficient Synthesis of Meningococcal X Polysaccharide Repeating Unit (N-Acetylglucosamine-4-phosphate) as Analytical Standard for Polysaccharide Determination

  摘要：

  Serogroup X Neisseria meningitidis (MenX) is emerging in many African countries as a major cause of meningococcal meningitis, but no preventative therapy against this serogroup is yet available. N-Acetylglucosamine-4-phosphate (4P-GlcNAc), the monomeric repeating unit of MenX polysaccharide, is an important requirement for the development of an analytical method specific for MenX polysaccharide quantification. At the moment, this compound is not commercially available. Herein an efficient preparation of this monosaccharide is reported.

  DOI：

  10.1080/00397911.2013.853189

文献信息

• Efficient Synthesis of Meningococcal X Polysaccharide Repeating Unit (N-Acetylglucosamine-4-phosphate) as Analytical Standard for Polysaccharide Determination
  作者：Roberto Adamo、Francesca Micoli、Daniela Proietti、Francesco Berti

  DOI：10.1080/00397911.2013.853189

  日期：2014.5.3

  Serogroup X Neisseria meningitidis (MenX) is emerging in many African countries as a major cause of meningococcal meningitis, but no preventative therapy against this serogroup is yet available. N-Acetylglucosamine-4-phosphate (4P-GlcNAc), the monomeric repeating unit of MenX polysaccharide, is an important requirement for the development of an analytical method specific for MenX polysaccharide quantification. At the moment, this compound is not commercially available. Herein an efficient preparation of this monosaccharide is reported.