1,3,4,6-tetra-O-acetyl-2-deoxy-2-<3-(4-tolylureido)>-β-D-glucopyranose | 4710-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-<3-(4-tolylureido)>-β-D-glucopyranose
• 英文别名: N-(p-methylphenyl)-N'-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranos-2-yl)urea；N-(1,3,4,6-tetra-O-acetyl)-2-deoxy-β-D-glucosyl-N’-(4-methylphenyl)urea；[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[(4-methylphenyl)carbamoylamino]oxan-2-yl]methyl acetate
• CAS: 4710-56-9
• 化学式: C₂₂H₂₈N₂O₁₀
• 分子量: 480.472
• InChiKey: GQJPSMVTTLFAEL-PFAUGDHASA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  570.0±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-<3-(4-tolylureido)>-β-D-glucopyranose 在 氨 作用下， 以 甲醇 为溶剂， 生成 2-deoxy-2-<3-(4-tolylureido)>-β-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
• 作为产物：
  描述：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-2-<3-(4-tolylureido)>-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Novel Glycosyl Imidazolidine-2,4,5-Trione Derivatives

  摘要：

  通过缩合过-O-乙酰化氨基葡萄糖、三光气、胺和草酰氯，制备了一系列糖基咪唑烷-2,4,5-三酮衍生物。这种简便高效的方法可以得到所需的产物，而且收率极高。所有化合物都获得了令人满意的红外光谱、1H NMR、13C NMR 和 ESI-MS 图谱。

  DOI：

  10.14233/ajchem.2015.16824

文献信息

• 乙酰氨基葡萄糖基咪唑-2,4,5-三酮的合成方法 与抑菌用途
  申请人：淮海工学院

  公开号：CN103626816B

  公开（公告）日：2016-04-13

  本发明是一种乙酰氨基葡萄糖基咪唑-2,4,5-三酮。本发明还公开了乙酰氨基葡萄糖基咪唑-2,4,5-三酮的合成方法与用途。本发明合成方法是一种快速，高效，产率高的方法，在合成乙酰氨基葡萄糖基咪唑-2,4,5-三酮以市售氨基葡萄糖盐酸盐、固体光气、芳胺类和草酰氯为原料，原料廉价易得，降低了成本；反应条件采用传统加热模式，实验步骤简单，后处理简便环保，拓宽了该方法的适用范围；采用廉价易得原料作为反应物，降低了成本；在合成的目标化合物中引入乙酰氨基葡萄糖基团，有望得到生物活性更高的物质；合成的目标化合物对大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌均有较好的抑菌效果。
• 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。
• The reaction of 2-amino-2-deoxyhexopyranoses with isocyanates. Synthesis of ureas and their transformation into heterocyclic derivatives.
  作者：Martin Avalos、Reyes Babiano、Pedro Cintas、José L. Jiménez、Juan C. Palacios、Concepción Valencia

  DOI：10.1016/s0040-4020(01)86344-4

  日期：1993.3

  acidic pH values, whereas in neutral or basic media 5-hydroxyimidazolidin-2-one derivatives 66 can be isolated. These monocyclic structures appear to be the true intermediates of the reaction and, under appropriate conditions, can be converted exclusively into the corresponding cis-fused five-membered ring systems. Likewise, the first cis-fused glycopyrano[2,1-d]imidazolidin-2-ones 75 have been also prepared

  已经详细研究了2-氨基-2-脱氧甘露糖醛糖与异氰酸芳基酯的反应，并获得了脲和杂环衍生物。糖基呋喃并[ 2，1- d ]咪唑烷基-2-酮62的形成机理现已变得可见，而先前的报道和涉及该主题的经典文献提出了反应产物的替代结构。该反应是pH依赖性的，在酸性pH值下仅能平稳地获得呋喃酮类自行车，而在中性或碱性介质中，可以分离出5-羟基咪唑啉-2-酮衍生物66。这些单环结构似乎是反应的真正中间体，并且在适当的条件下，可以独家转化为相应的顺式融合的五元环系统。同样，还制备了第一个顺式融合的吡喃并[ 2，1- d ]咪唑烷基-2-酮75。
• New synthetic approaches to sugar ureas. Access to ureido-β-cyclodextrins
  作者：Óscar López、Susana Maza、Inés Maya、José Fuentes、José G. Fernández-Bolaños

  DOI：10.1016/j.tet.2005.07.041

  日期：2005.9

  An efficient method for the preparation of urea-bridged cyclodextrins using triphosgene in the isocyanation step in an aqueous two-phase system is reported. Per-O-acetylated glycopyranosylamines and 2-amino-2-deoxy-alpha and beta-D-glucose were also transformed into the corresponding isocyanates using either an aqueous two-phase or an anhydrous dichloromethane medium, and converted in situ into ureas. An alternative method for the preparation of sugar-derived ureas consisting of desulfurization of sugar thioureas with mercury oxide is also presented. (c) 2005 Elsevier Ltd. All rights reserved.
• A facile access to ureido sugars. Synthesis of urea-bridged β-cyclodextrins
  作者：Inés Maya、Óscar López、Susana Maza、José G. Fernández-Bolaños、José Fuentes

  DOI：10.1016/j.tetlet.2003.09.140

  日期：2003.11

  The preparation of a urea-bridged beta-cyclodextrin dimer and of a 6-monodeoxy-6-mono[3-(beta-D-glucopyranos-2-yl)ureido]-beta-cyclodextrin has been developed, using triphosgene as the isocyanation agent in an aqueous two-phase system. Per-O-acetylated beta-D-gluco and mannopyranosylamines and 2-amino-2-deoxy-alpha- and beta-D-glucose were also transformed into the corresponding isocyanates and converted in situ into ureas by coupling with aromatic and aliphatic amines. (C) 2003 Elsevier Ltd. All rights reserved.