N,N-diethyl-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea | 260350-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-diethyl-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(diethylcarbamothioylamino)oxan-2-yl]methyl acetate
• CAS: 260350-43-4
• 化学式: C₁₉H₃₀N₂O₉S
• 分子量: 462.521
• InChiKey: BHNRNIXTKYVJRY-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea 在 mercury(II) oxide 作用下， 以 水 、 乙腈 为溶剂， 反应 40.0h， 以72%的产率得到N,N-diethyl-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)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-β-D-glucopyranosylamine hydrobromide 在 calcium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 N,N-diethyl-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 OF 6-SUBSTITUTED 5-AZAURIDINES AND THEIR PYRANOSE-TYPE NUCLEOSIDES BY CYCLODESULFURIZATION OF GLYCOSYL THIOUREAS
  作者：Yasuo Gama、Isao Shibuya、Masao Shimizu、Midori Goto

  DOI：10.1081/car-100106929

  日期：2001.7.31

  Cyclodesulfurization of N,N,N'-trisubstituted glycosyl thioureas with silver cyanate in acetonitrile for 5 h at 50 degreesC gave 1-glycosyl 5-azauracil derivatives as nucleoside analogues in good yields. The structures were determined by spectroscopic and X-Ray analyses and the reaction mechanism is discussed.