N,N'-bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea | 6983-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N'-bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea
• 英文别名: N,N'-bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea；N.N'-Bis--thioharnstoff；N.N'-Bis-(tetra-O-acetyl-β-D-glucosyl)-thioharnstoff；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]carbamothioylamino]oxan-2-yl]methyl acetate
• CAS: 6983-37-5
• 化学式: C₂₉H₄₀N₂O₁₈S
• 分子量: 736.705
• InChiKey: HQXVZJGPEKDKJC-QACPWNKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  285
• 氢给体数：
  2
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  N,N'-bis-(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 24.0h， 以68%的产率得到N,N'-di-β,β-2,3,4,6-octa-O-acetyl-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：

  乙酰溴葡糖 在 对硝基苯酚 、 三乙胺 作用下， 以 xylene 、 苯 为溶剂， 反应 2.0h， 生成 N,N'-bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea
  参考文献：
  名称：

  Petushkova, S. G.; Pavlov, A. E.; Sokolov, V. M., Russian Journal of General Chemistry, 1993, vol. 63, # 5.2, p. 792 - 795

  摘要：

  DOI：

文献信息

• Synthesis of Thioureido-Linked Peptidomimetics, Glycosylated Amino Acids, and Neoglycoconjugates Using Bis(benzotriazolyl)methanethione as Thioacylating Agent
  作者：Vommina Sureshbabu、Gundala Chennakrishnareddy、Hosahalli Hemantha

  DOI：10.1055/s-0029-1219393

  日期：2010.3

  A practical synthesis of thiourea-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates is described employing bis(benzotriazolyl)methanethione as thiocarbonylating reagent. The entire protocol is mild, efficient, high-yielding, and free from hazardous reagents. All the intermediates and products have been isolated and fully characterized by ¹H NMR, ¹³C NMR, and mass spectrometry.

  本文描述了一种实用的硫脲连接肽模拟物、糖基化氨基酸和新生糖缀合物的综合合成方法，采用双（苯并三唑基）甲烷硫酮作为硫羰基化试剂。整个方案温和、高效、产率高，并且不含危险试剂。所有中间体和产物均已分离并通过¹H NMR、¹³C NMR 和质谱完全表征。
• An Expedient Synthesis of Novel<i>N,N′</i>-Diglycosylguanidine Derivatives in the Presence of Hg(II)
  作者：Hong-Mei Chen、Gen Li、Ling-Hua Cao

  DOI：10.1002/jccs.200800071

  日期：2008.4

  The reactions of N,N'-diglycosythiourea with 2-amino-benzothiazoles in the presence of Hg(II) (HgCl 2 or HgO) for the synthesis of N-(4/6-substituted-benzothiazol-2-yl)-N',N"-diglycosylguanidines have been reported.

  N,N'-二糖基硫脲与 2-氨基苯并噻唑在 Hg(II)（HgCl 2 或 HgO）存在下反应合成 N-(4/6-取代的苯并噻唑-2-基)-N ',N'-二糖基胍已被报道。
• Blanco, Jose L. Jimenez; Barria, Claudio Saitz; Benito, Juan M., Synthesis, 1999, # 11, p. 1907 - 1914
  作者：Blanco, Jose L. Jimenez、Barria, Claudio Saitz、Benito, Juan M.、Mellet, Carmen Ortiz、Fuentes, Jose、Santoyo-Gonzales, Francisco、Fernandez, Jose M. Garcia

  DOI：——

  日期：——
• A new method for the preparation of acylated glycosylamines and their transformations into glycosyl isothiocyanates and N,N′-diglycosylthioureas
  作者：Reyes Babiano Caballero、Jose Fuentes Mota、Juan Antonio Galbis Perez

  DOI：10.1016/s0008-6215(00)90042-9

  日期：1986.10