2,3,4,6-tetra-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine | 22435-64-9

• 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: 2,3,4,6-tetra-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine
• 英文别名: 2,3,4,6-Tetra-O-acetyl-N-<2,2-bis-aethoxycarbonyl-vinyl>-β-D-glucopyranosylamin；2,3,4,6-Tetra-O-acetyl-N-(2,2-bis-aethoxycarbonyl-vinyl)-β-D-glucopyranosylamin；diethyl 2-[[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]methylidene]propanedioate
• CAS: 22435-64-9
• 化学式: C₂₂H₃₁NO₁₃
• 分子量: 517.487
• InChiKey: TVUGVZHSQMAKLJ-OUUBHVDSSA-N

物化性质

• 沸点：
  546.2±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  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 为溶剂， 反应 2.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate
  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：

  N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 、 乙酸酐 在 吡啶 作用下， 生成 2,3,4,6-tetra-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  糖异氰酸酯的合成及其在形成脲基双糖中的应用

  摘要：

  目前的工作描述了一种简便实用的基于碳水化合物的异氰酸酯的途径，这是一种反应性和吸引人的手性杂草烯家族，可以很容易地转化为通过尿素部分相互连接的二糖和假二糖。通过 X 射线衍射分析和光谱方法对这些物质进行全面表征，可以进一步了解它们的结构和优选构象。

  DOI：

  10.1002/ejoc.200500601

文献信息

• A facile access to ureido sugars. Synthesis of urea-bridged β-cyclodextrins
  作者：Inés Maya、Óscar López、Susana Maza、José G. Fernández-Bolaños、José Fuentes

  DOI：10.1016/j.tetlet.2003.09.140

  日期：2003.11

  The preparation of a urea-bridged beta-cyclodextrin dimer and of a 6-monodeoxy-6-mono[3-(beta-D-glucopyranos-2-yl)ureido]-beta-cyclodextrin has been developed, using triphosgene as the isocyanation agent in an aqueous two-phase system. Per-O-acetylated beta-D-gluco and mannopyranosylamines and 2-amino-2-deoxy-alpha- and beta-D-glucose were also transformed into the corresponding isocyanates and converted in situ into ureas by coupling with aromatic and aliphatic amines. (C) 2003 Elsevier Ltd. All rights reserved.
• 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
• A one-pot domino reaction in constructing isoorotate bases and their nucleosides
  作者：Martín Avalos、Reyes Babiano、Pedro Cintas、Michael B. Hursthouse、José L. Jiménez、Encarnación Lerma、Mark E. Light、Juan C. Palacios

  DOI：10.1016/j.tetlet.2006.01.057

  日期：2006.3

  A novel strategy, involving the coupling of enaminoesters with chlorosulfonyl isocyanate and accelerated by microwave irradiation, enables the straightforward preparation of the biologically important isoorotate bases. Extensions to nucleoside derivatives are also described. (c) 2006 Elsevier Ltd. All rights reserved.
• BABIANO, REYES;DURAN, CARLOS;PLUMET, JOAQUIN;ROMAN, EMILIO;SANCHEZ, ELOIS+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N1, C. 1923-1926
  作者：BABIANO, REYES、DURAN, CARLOS、PLUMET, JOAQUIN、ROMAN, EMILIO、SANCHEZ, ELOIS+

  DOI：——

  日期：——