N-acetyl-N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea | 866416-49-1

• 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: N-acetyl-N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[acetyl-(4-methylphenyl)carbamothioyl]amino]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 866416-49-1
• 化学式: C₂₄H₃₀N₂O₁₀S
• 分子量: 538.576
• InChiKey: MLYGSHWEFXVHHG-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  37
• 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：
  179
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-acetyl-N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea 在 咪唑 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以86%的产率得到N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea
  参考文献：
  名称：

  New synthetic approaches to sugar ureas. Access to ureido-β-cyclodextrins

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.07.041
• 作为产物：
  描述：

  乙酸酐 、 N-(β-D-glucopyranosyl)-N'-(p-methylphenyl)thiourea 在 吡啶 作用下， 反应 24.0h， 以73%的产率得到N-acetyl-N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea
  参考文献：
  名称：

  New synthetic approaches to sugar ureas. Access to ureido-β-cyclodextrins

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.07.041

文献信息

• Synthesis and characterization of mercury(II)–sugar thioureas complexes
  作者：Susana Maza、Óscar López、Inés Maya、José G. Fernández-Bolaños

  DOI：10.1016/j.poly.2009.09.006

  日期：2009.12

  The synthesis of a novel class of mercury(II) complexes with sugar-derived bidentade isothioureido ligands, by treatment of N-acylated thioureas with an excess of yellow mercury(II) oxide in aqueous acetonitrile is reported. The 1:2 coordination stoichiometry of the complexes were confirmed by elemental analysis, mass spectrometry and NMR spectroscopy, and they were found to be consistent with a four-coordinate geometry. (C) 2009 Elsevier Ltd. All rights reserved.