2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside | 886050-86-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside
• 英文别名: [(2S,3S,4S,5R,6R)-2-(2-azidoethoxy)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]-5-phenylmethoxyoxan-3-yl] 4-oxopentanoate
• CAS: 886050-86-8
• 化学式: C₄₄H₅₃N₃O₉Si
• 分子量: 796.005
• InChiKey: ISPOLSRBINCLPR-HVJQSLJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  57
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  Synthesis of 2-azidoethyl α-d-mannopyranoside orthogonally protected and selective deprotections

  摘要：

  We present the synthesis of a fully orthogonally protected mannosyl glycoside I and the corresponding methods for selective deprotections. Mannosyl glycoside I contains a functionalized linker at the anomeric position to allow for the attachment of carbohydrate units to scaffolds in order to prepare carbohydrate multivalent systems. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.063
• 作为产物：
  描述：

  2-azidoethyl α-D-mannopyranoside 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of 2-azidoethyl α-d-mannopyranoside orthogonally protected and selective deprotections

  摘要：

  We present the synthesis of a fully orthogonally protected mannosyl glycoside I and the corresponding methods for selective deprotections. Mannosyl glycoside I contains a functionalized linker at the anomeric position to allow for the attachment of carbohydrate units to scaffolds in order to prepare carbohydrate multivalent systems. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.063

文献信息

• Docking, synthesis, and NMR studies of mannosyl trisaccharide ligands for DC-SIGN lectin
  作者：José J. Reina、Irene Díaz、Pedro M. Nieto、Nuria E. Campillo、Juan A. Páez、Georges Tabarani、Franck Fieschi、Javier Rojo

  DOI：10.1039/b802144a

  日期：——

  DC-SIGN, a lectin, which presents at the surface of immature dendritic cells, constitutes nowadays a promising target for the design of new antiviral drugs. This lectin recognizes highly glycosylated proteins present at the surface of several pathogens such as HIV, Ebola virus, Candida albicans, Mycobacterium tuberculosis, etc. Understanding the binding mode of this lectin is a topic of tremendous interest and will permit a rational design of new and more selective ligands. Here, we present computational and experimental tools to study the interaction of di- and trisaccharides with DC-SIGN. Docking analysis of complexes involving mannosyl di- and trisaccharides and the carbohydrate recognition domain (CRD) of DC-SIGN have been performed. Trisaccharides Manα1,2[Manα1,6]Man 1 and Manα1,3[Manα1,6]Man 2 were synthesized from an orthogonally protected mannose as a common intermediate. Using these ligands and the soluble extracellular domain (ECD) of DC-SIGN, NMR experiments based on STD and transfer-NOE were performed providing additional information. Conformational analysis of the mannosyl ligands in the free and bound states was done. These studies have demonstrated that terminal mannoses at positions 2 or 3 in the trisaccharides are the most important moiety and present the strongest contact with the binding site of the lectin. Multiple binding modes could be proposed and therefore should be considered in the design of new ligands.

  DC-SIGN是一种存在于未成熟树突状细胞表面的凝集素，如今成为设计新型抗病毒药物的有前景的目标。这种凝集素识别存在于多种病原体表面的高度糖基化蛋白，如HIV、埃博拉病毒、白色念珠菌、结核分枝杆菌等。了解这种凝集素的结合模式是一个极为有趣的话题，将允许合理设计新型且更具选择性的配体。在此，我们介绍了用于研究二糖和三糖与DC-SIGN相互作用的计算和实验工具。已经进行了涉及甘露糖基二糖和三糖以及DC-SIGN的碳水化合物识别域（CRD）的复合物的对接分析。三糖Manα1,2[Manα1,6]Man 1和Manα1,3[Manα1,6]Man 2是从一个正交保护的甘露糖作为共同中间体合成的。使用这些配体和可溶性胞外域（ECD）的DC-SIGN，基于STD和transfer-NOE的NMR实验提供了额外的信息。进行了甘露糖基配体在自由和结合状态下的构象分析。这些研究表明，三糖中位置2或3的末端甘露糖是最重要的部分，并且与凝集素的结合位点呈现最强的接触。可以提出多种结合模式，因此在设计新配体时应予以考虑。
• Synthesis of 2-azidoethyl α-d-mannopyranoside orthogonally protected and selective deprotections
  作者：José Juan Reina、Javier Rojo

  DOI：10.1016/j.tetlet.2006.02.063

  日期：2006.4

  We present the synthesis of a fully orthogonally protected mannosyl glycoside I and the corresponding methods for selective deprotections. Mannosyl glycoside I contains a functionalized linker at the anomeric position to allow for the attachment of carbohydrate units to scaffolds in order to prepare carbohydrate multivalent systems. (c) 2006 Elsevier Ltd. All rights reserved.