2-methyl-3-allyloxycarbonyl-(3,4,6-tri-O-acetyl-1,2-didesoxy-α-D-glucopyrano)<2,1-d>-1-imidazoline | 142544-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-allyloxycarbonyl-(3,4,6-tri-O-acetyl-1,2-didesoxy-α-D-glucopyrano)<2,1-d>-1-imidazoline
• 英文别名: prop-2-enyl (3aS,5R,6S,7R,7aR)-6,7-diacetyloxy-5-(acetyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]imidazole-1-carboxylate
• CAS: 142544-01-2
• 化学式: C₁₈H₂₄N₂O₉
• 分子量: 412.397
• InChiKey: UWLVIRMIOOJXCO-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-methyl-3-allyloxycarbonyl-(3,4,6-tri-O-acetyl-1,2-didesoxy-α-D-glucopyrano)<2,1-d>-1-imidazoline 在 四(三苯基膦)钯 盐酸 、 甲酸 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 52.0h， 生成 2-methyl-4-(1',2',3',4'-tetrahydroxybutyl)imidazole
  参考文献：
  名称：

  α-Glucopyranoimidazolines as intermediate analogue inhibitors of family 20 β-N-acetylglucosaminidases

  摘要：

  The alpha-glucopyranoimidazolines, 2-methyl-(1,2-dideoxy-alpha-D-glucopyrano)[2,1-d]-1-imidazolines 1 and 2, have been synthesized and evaluated as inhibitors of beta-N-acetylglucosaminidases (NAGs). Compounds I and 2, mimicking the oxazolinium ion intermediate in enzyme catalysis, served as potent and competitive inhibitors of family 20 NAGs with K-i as low as 0.1 muM, but showed no inhibitory activities toward family 3 NAGs. Due to structural and electrostatic resemblance to the oxazolinium ion intermediate, the alpha-glucopyranoimidazolines may lead to novel and selective inhibitors of mechanistically related glycosidases such as family 18 chitinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.017
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose 、 乙腈 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以99%的产率得到2-methyl-3-allyloxycarbonyl-(3,4,6-tri-O-acetyl-1,2-didesoxy-α-D-glucopyrano)<2,1-d>-1-imidazoline
  参考文献：
  名称：

  Glycosylations with tetra-O-acetyl-N-allyloxycarbonylamino-2-deoxy-β-D-glucose in polar solvents

  摘要：

  Glycosylations with the title compound were performed in dimethylformamide, acetonitrile, and nitromethane. The latter solvent was found to give good results whereas DMF caused 1-O-deacetylation.

  DOI：

  10.1016/s0040-4020(01)92269-0