N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea | 105014-62-8

• 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'-(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-[(4-methylphenyl)carbamothioylamino]oxan-2-yl]methyl acetate
• CAS: 105014-62-8
• 化学式: C₂₂H₂₈N₂O₉S
• 分子量: 496.538
• InChiKey: VTUFZMAZTPJIEJ-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  171
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(p-methylphenyl)-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 24.0h， 以74%的产率得到N-(p-methylphenyl)-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：

  4-甲基苯胺盐酸盐 在 镍 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.5h， 生成 N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea
  参考文献：
  名称：

  Ali, M. Umar; Meshram, H. M.; Paranjpe, M. G., Journal of the Indian Chemical Society, 1985, vol. 62, # 9, p. 666 - 669

  摘要：

  DOI：

文献信息

• Novel and Efficient Synthesis of 4-Dimethylamino-2-glycosylaminoquinazolines by Cyclodesulfurization of Glycosyl Thioureas with Dimethylcyanamide.
  作者：Yasuo Gama、Isao Shibuya、Masao Shimizu

  DOI：10.1248/cpb.50.1517

  日期：——

  4-Dimethylamino-2-glycosylaminoquinazoline derivatives were synthesized by cyclodesulfurization of N-aryl-N′-glycosyl thioureas with dimethylcyanamide in the presence of silver triflate in good yields.

  在三酸银存在下，通过 N-芳基-N′-糖基硫脲与二甲基氰酰胺的环去硫化反应，合成了 4-二甲基氨基-2-糖基氨基喹唑啉衍生物，产率良好。
• Preparation of glycosyl thiourea derivatives from glycosyl azides using sulfamic acid and sodium iodide in one-pot
  作者：Arin Gucchait、Manas Jana、Kuladip Jana、Anup Kumar Misra

  DOI：10.1016/j.carres.2016.09.002

  日期：2016.11

  Novel one-pot reaction conditions have been developed for the preparation of glycosyl thiourea derivatives directly from glycosyl azides mediated by a combination of sulfamic acid and sodium iodide. The reaction conditions were clean, non-toxic and the products were isolated in good to excellent yield.

  已经开发了新颖的一锅法反应条件，用于直接由氨基磺酸和碘化钠的组合介导的糖基叠氮化物制备糖基硫脲衍生物。反应条件是干净，无毒的，并且以良好至优异的产率分离了产物。
• Yadgire, Atul V.; Korpe, Gajanan V.; Deshmukh, Shirish P., E-Journal of Chemistry, 2011, vol. 8, # 4, p. 1614 - 1619
  作者：Yadgire, Atul V.、Korpe, Gajanan V.、Deshmukh, Shirish P.

  DOI：——

  日期：——
• SHEROVA, M. A.;SARYMZAKOVA, R. K.;TKACHEVA, A. P.;DZHAMANBAEVA, Z. A., 1988) 8 S., KIRGNIINTI, 399-KI88
  作者：SHEROVA, M. A.、SARYMZAKOVA, R. K.、TKACHEVA, A. P.、DZHAMANBAEVA, Z. A.

  DOI：——

  日期：——