dodecyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside | 196697-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: dodecyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• CAS: 196697-98-0
• 化学式: C₂₃H₄₃NO₆
• 分子量: 429.598
• InChiKey: MEMKRYHSISUSSJ-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dodecyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 在 N-羟基丁二酰亚胺 、 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 3.25h， 生成 O-(dodecyl 2-acetamido-2,3-dideoxy-β-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：

  十二烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷 在 甲醇 、 2-甲基苯磺酸 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 dodecyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-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