dodecyl 2-acetamido-2-deoxy-α-D-glucopyranoside | 147025-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodecyl 2-acetamido-2-deoxy-α-D-glucopyranoside
• 英文别名: Dodecyl 2-(acetylamino)-2-deoxy-I+/--D-glucopyranoside；N-[(2S,3R,4R,5S,6R)-2-dodecoxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 147025-04-5
• 化学式: C₂₀H₃₉NO₆
• 分子量: 389.533
• InChiKey: YNPQAQWLYWACJR-WAPOTWQKSA-N

物化性质

• 熔点：
  144-145 °C
• 沸点：
  592.5±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  27.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  108.25
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dodecyl 2-acetamido-2-deoxy-α-D-glucopyranoside 在 2-甲基苯磺酸 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine

  摘要：

  Anomeric pairs of alpha- and beta-dodecyl, alpha- and beta-(1-pentylhexyl), and alpha- and beta-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting beta-D-glucosaminides were obtained by the oxazoline method, and the corresponding alpha-isomers, by the mercuric iodide-catalyzed glycosylation of alcohols with alpha-glucosaminyl chloride peracetate in nitromethane at -90 degrees C. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 mu g/mouse) and Escherichia coli (doses of 0.05, 1, and 20 mu g/mouse) with the MDP alpha- and beta-glycosides were found.

  DOI：

  10.1134/s1068162006040091
• 作为产物：
  描述：

  dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 16.0h， 以95%的产率得到dodecyl 2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine

  摘要：

  Anomeric pairs of alpha- and beta-dodecyl, alpha- and beta-(1-pentylhexyl), and alpha- and beta-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting beta-D-glucosaminides were obtained by the oxazoline method, and the corresponding alpha-isomers, by the mercuric iodide-catalyzed glycosylation of alcohols with alpha-glucosaminyl chloride peracetate in nitromethane at -90 degrees C. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 mu g/mouse) and Escherichia coli (doses of 0.05, 1, and 20 mu g/mouse) with the MDP alpha- and beta-glycosides were found.

  DOI：

  10.1134/s1068162006040091