cyclododecyl 2-acetamido-2-deoxy-α-D-glucopyranoside | 941302-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclododecyl 2-acetamido-2-deoxy-α-D-glucopyranoside
• CAS: 941302-97-2
• 化学式: C₂₀H₃₇NO₆
• 分子量: 387.517
• InChiKey: QNJAPEZVVIFQQN-WAPOTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• 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：

  cyclododecyl 2-acetamido-2-deoxy-α-D-glucopyranoside 在 N-羟基丁二酰亚胺 、 2-甲基苯磺酸 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.25h， 生成 O-(cyclododecyl 2-acetamido-2,3-dideoxy-α-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester
  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：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 甲醇 、 3 A molecular sieve 、 sodium methylate 、 mercury(II) iodide 作用下， 以 硝基甲烷 为溶剂， 反应 17.5h， 生成 cyclododecyl 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