1-N-benzoyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine | 18918-50-8

• 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: 1-N-benzoyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
• 英文别名: 2,3,4,6-tetra-O-acetyl-N-benzoyl-β-D-glucopyranosylamine；N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzamide；N-benzoyltetra-O-acetyl-β-D-glucopyranosylamin；Tetra-O-acetyl-N-benzoyl-β-D-glucopyranosylamin；N-(Tetraacetyl-1-β-D-glucopyranosyl)-benzamid；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-benzamidooxan-2-yl]methyl acetate
• CAS: 18918-50-8
• 化学式: C₂₁H₂₅NO₁₀
• 分子量: 451.43
• InChiKey: HTKGZSJIRHIVAV-GQUPQBGVSA-N

物化性质

• 熔点：
  190-192 °C
• 沸点：
  582.6±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-N-benzoyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到β-1-N-benzamido-D-glucopyranose
  参考文献：
  名称：

  使用硒代羧酸酯作为形成酰胺键的无痕迹试剂合成糖基酰胺

  摘要：

  从包括呋喃糖基和吡喃糖基衍生物在内的多种底物成功成功地制备了碳水化合物衍生的酰胺。该方法学成功地依赖于从Se / LiEt 3 BH和酰基氯或羧酸中原位生成硒酸锂锂，以及它们与糖叠氮化物的反应。本协议的一个关键方面是我们从元素硒开始。避免了所有反应性和敏感的含硒中间体的分离和处理，因此提供了硒代羧酸盐无痕试剂的状态。

  DOI：

  10.1021/acs.joc.6b00832
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium azide 、 四丁基硫酸氢铵 、 碳酸氢钠 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 1-N-benzoyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
  参考文献：
  名称：

  碳水化合物基支架的开发，用于限制识别基团的表达。二价配体的扩展及其对二聚受体结构的影响。

  摘要：

  已经通过NMR研究了糖基酰胺的溶液结构。与以Z-抗结构为主的仲芳族糖基酰胺相反，叔芳族糖基酰胺显示出对E-抗结构的强烈偏好。这些种类的分子表现出的结构多样性似乎很重要，因为芳香环或与芳香环相连的基团的方向性可以通过选择在异头中心处具有仲酰胺或叔酰胺来确定，并且可以在设计具有碳水化合物支架的生物活性分子时应予以考虑。还对相关的二价仲和叔糖基酰胺进行了结构分析，这些化合物显示出与单价化合物相似的偏好。受约束的二价化合物具有促进将形成具有受限结构的簇的潜力，因此对于多价配体的作用机理的新颖研究具有潜力。此类化合物的可能应用将用作支架的设计和合成，以促进蛋白质-蛋白质或其他受体-受体相互作用。设计成与识别碳水化合物的蛋白结合的限制性二价（或更高阶）配体的亲和力，其亲和力可能明显高于没有这些特性的单价对应物或多价配体，而后者会促进成簇并同时促进蛋白质-蛋白质相互作用。这可能是开发基于碳水化合物的疗法的一种新方法。

  DOI：

  10.1021/jo034336d

文献信息

• An easy access to anomeric glycosyl amides and imines(Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides
  作者：László Kovács、Erzsébet Ősz、Valéria Domokos、Wolfgang Holzer、Zoltán Györgydeák

  DOI：10.1016/s0040-4020(01)00380-5

  日期：2001.5

  The preparation and application of anomeric glycosyl phosphinimides in preparative synthesis were studied. Starting from the appropriate glycosyl azides and trialkyl or triaryl phosphines, the corresponding phosphinimides were obtained by modified Staudinger reactions. The latter compounds were readily converted into 1-N-acyl-gluco- and galactopyranosyl amines with high yields by applying activated

  研究了异头糖基次膦酰亚胺的制备及在合成中的应用。从合适的糖基叠氮化物和三烷基或三芳基膦开始，通过改良的施陶丁格反应获得相应的亚膦酰亚胺。通过使用活化的酸衍生物或简单的羧酸，后一种化合物容易以高收率转化成1 - N-酰基-葡萄糖-和吡喃半乳糖基胺。通过氮杂-维蒂希反应分别使用脂族或芳族醛，获得1- N-亚烷基-亚芳基次膦酸酯或席夫碱（席夫碱）。
• Synthesis of Glucopyranosyl Amides Using Polymer‐Supported Reagents
  作者：Yuriko Y. Root、Maximillian S. Bailor、Peter Norris

  DOI：10.1081/scc-120039504

  日期：2004.1.1

  Abstract 2,3,4,6‐Tetra‐O‐acetyl‐β‐D‐glucopyranosyl azide reacts efficiently with polymer‐supported triphenylphosphine and various acid chlorides to yield glucopyranosyl amides with retention of the β‐gluco stereochemistry.

  摘要 2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基叠氮化物与聚合物负载的三苯基膦和各种酰氯有效反应，生成保留β-葡萄糖立体化学的吡喃葡萄糖基酰胺。
• Synthesis of a glucuronic acid and glucose conjugate library and evaluation of effects on endothelial cell growth
  作者：Nigel Pitt、Rhona M. Duane、Alan O' Brien、Helena Bradley、Stephen J. Wilson、Kathy M. O' Boyle、Paul V. Murphy

  DOI：10.1016/j.carres.2004.05.024

  日期：2004.8

  Compounds that alter endothelial cell growth are of interest in the development of angiogenesis modulators. A structurally diverse series of saccharide derivatives (glycosylamide conjugates) have been synthesized and evaluated for their effects on bovine aortic endothelial cell (BAEC) growth. Heparin-albumin (HA) reduced BAEC growth by 32% at 10 mug/mL and a number of the novel saccharide conjugates from the library were found to mimic the effect of HA as they also inhibit endothelial cell survival under identical conditions. Two thiophene conjugates, thioglucamide (24% inhibition at 35 muM) and a related glucuronide (26% inhibition at 33 muM) were the most potent inhibitors of BAEC growth, as determined using a methylthiazol tetrazoliurn (MTT) assay. The effects of thioglucamide and HA on absolute cell number were also studied using cell counting experiments; thioglucamide (47% after 24 h) was more potent than indicated by the MTT assay and initially reduced the BAEC number to a greater extent than HA (30% after 24 h); however, its actions were over more rapidly than were HA's as cell growth had returned to levels of the control after 72 h where HA still caused 25% inhibition. The binding of the monosaccharide conjugates to fibroblast growth factor (FGF-2) in competition with heparin-alburnin by ELISA was investigated to establish the possible mechanism by which glycoconjugates could alter growth but there was no general correlation between reduction in viable cell population and binding to FGF-2. No glycoconjugate reduced the proliferation of mouse mammary epithelial cells, nor did any alter gross cell morphology, supporting a proposal that the reduction in BAEC survival by monosaccharide conjugates such as thioglucamide is a result of the inhibition of cell proliferation rather than being an induction of cytotoxicity. These studies indicate that cell biological studies to determine the mechanism of action of the simple monosaccharide conjugates may be worthwhile. (C) 2004 Elsevier Ltd. All rights reserved.
• Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case
  作者：Evangelia D. Chrysina、Éva Bokor、Kyra-Melinda Alexacou、Maria-Despoina Charavgi、George N. Oikonomakos、Spyros E. Zographos、Demetres D. Leonidas、Nikos G. Oikonomakos、László Somsák

  DOI：10.1016/j.tetasy.2009.03.021

  日期：2009.5

  Per-O-acetylated beta-D-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-beta-D-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(beta-D-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions. Deprotection of these products by the Zemplen method furnished beta-D-Glc(p)-NHCO-R derivatives as well as 1-(beta-D-Glc(p))-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme-inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided. (C) 2009 Elsevier Ltd. All rights reserved.
• Application of bis(diphenylphosphino)ethane (DPPE) in Staudinger-type N-glycopyranosyl amide synthesis
  作者：David P. Temelkoff、Craig R. Smith、Daniel A. Kibler、Shawn McKee、Sara J. Duncan、Matthias Zeller、Mo Hunsen、Peter Norris

  DOI：10.1016/j.carres.2006.02.001

  日期：2006.7

  Bis(diphenylphosphino)ethane (DPPE) reacts with pyranosyl azides derived from D-glucose and D-glucuronic acid in the presence of acid chlorides to yield the corresponding glycosyl amides. Reaction rates are comparable to those with triphenylphosphine, however, the byproduct phosphine oxide is easily removed from reaction mixtures using column chromatography. The simple and clean workup allows for the formation of collections of related compounds by parallel synthesis, and the method is also applicable to scaled-up reactions. The beta-stereochemistry of the glycosyl azide precursor is retained in all cases, which is supported by X-ray crystallography in several cases. (c) 2006 Elsevier Ltd. All rights reserved.