N-(p-methylphenyl)-N'-(1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranos-2-yl)thiourea | 866416-47-9

• 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: N-(p-methylphenyl)-N'-(1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranos-2-yl)thiourea
• CAS: 866416-47-9
• 化学式: C₂₂H₂₈N₂O₉S
• 分子量: 496.538
• InChiKey: QZGKGVYKRWMKOA-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  138.49
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-(p-methylphenyl)-N'-(1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranos-2-yl)thiourea 在 mercury(II) oxide 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以67%的产率得到N-(p-methylphenyl)-N'-(1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranos-2-yl)urea
  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：

  2,3,4,6-tetra-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 在 溴 、 calcium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 N-(p-methylphenyl)-N'-(1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranos-2-yl)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