2-deoxy-2-<3-(4-tolylureido)>-α-D-glucopyranose | 149117-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-<3-(4-tolylureido)>-α-D-glucopyranose
• 英文别名: N-(4-Methyl-phenylcarbamoyl)-α-D-glucosamin；1-(4-methylphenyl)-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
• CAS: 149117-44-2
• 化学式: C₁₄H₂₀N₂O₆
• 分子量: 312.323
• InChiKey: QQEIYMFJKWVPSX-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(p-methylphenyl)-N'-(1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranos-2-yl)urea 在 氨 作用下， 以 甲醇 为溶剂， 生成 2-deoxy-2-<3-(4-tolylureido)>-α-D-glucopyranose
  参考文献：
  名称：

  关于D-葡萄糖胺的脲和四氢咪唑衍生物

  摘要：

  描述了D-葡萄糖胺的脲，硫脲和四氢咪唑衍生物的合成。

  DOI：

  10.1002/hlca.19610440209

文献信息

• Synthesis and antifungal activity of d-glucopyranosyl ureas and d-glucofurano-imidazolidine-2-ones
  作者：Xuan Tang、Feng Xue、Hongju Ma、Xiufang Cao、Changshui Chen、Xuegang Li

  DOI：10.1007/s11164-012-0596-8

  日期：2013.3

  A series of N-β-d-glucopyranosyl-N’-substituted phenyl ureas were synthesized by reaction of glucosyl isocyanate with arylamines and glycosamine with aryl isocyanates, and a series of d-glucofurano-imidazolidine-2-ones were obtained via deacetylation of glycosylureas. Although some of the compounds have already been described, most were prepared for the first time in this work. The structures of all the compounds synthesized were confirmed by IR, 1H NMR, and, in part, by 13C NMR. Antifungal activity of the title compounds was determined against four kinds of plant pathogenic fungi, Sclerotinia sclerotiorum, Fusarium graminearum, Fusarium oxysporum, and Bipolaris maydis. Preliminary bioassay indicates that most of glycosylureas had some activity against S. sclerotiorum; for some, the antifungal activity was strong. However, most of the imidazolidine-2-ones had weak antifungal activity.

  通过葡萄糖基异氰酸酯与芳基胺和糖胺与芳基异氰酸酯的反应，合成了一系列 N-β-d-glucopyranosyl-N'-substituted phenyl 脲；通过糖基脲的脱乙酰化，得到了一系列 d-glucofurano-imidazolidine-2-one。虽然其中一些化合物已经被描述过，但大多数化合物都是在这项工作中首次制备的。所有合成化合物的结构都通过红外光谱、1H NMR 以及部分 13C NMR 进行了确认。测定了标题化合物对四种植物病原真菌--硬核菌、禾谷镰刀菌、氧孢镰刀菌和五月双孢蘑菇--的抗真菌活性。初步生物测定表明，大多数糖基脲类对硬菌有一定的活性；其中一些糖基脲类的抗真菌活性很强。然而，大多数咪唑烷-2-酮的抗真菌活性较弱。
• Über Harnstoff- und Tetrahydroimidazol-Derivate von D-Glucosamin
  作者：Ch. J. Morel

  DOI：10.1002/hlca.19610440209

  日期：——

  The synthesis of urea, thiourea and tetrahydroimidazole derivatives of D-glucosamine is described.

  描述了D-葡萄糖胺的脲，硫脲和四氢咪唑衍生物的合成。