propargyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside | 943859-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propargyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: 2′-propynyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside；(2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(prop-2-yn-1-yloxy)tetrahydro-2H-pyran-3,4-diyl diacetate；2-propynyl 2-N-acetoamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside；propargyl α-D-2-acetamido-2-deoxy-3,4,6-O-triacetylglucoside；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate
• CAS: 943859-74-3
• 化学式: C₁₇H₂₃NO₉
• 分子量: 385.371
• InChiKey: UAEPPSZVKZLPGJ-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  propargyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 Cu(I)-USY zeolite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以74%的产率得到2,6-di-O-(α-D-2-acetamido-2-deoxy-3,4,6-O-triacetylglucopyranosyl)hexa-2,4-diyn-1,6-diol
  参考文献：
  名称：

  铜沸石作为末端炔偶联的催化剂：二炔的有效合成

  摘要：

  CuI 改性的沸石，尤其是 CuI-USY，被证明是非常有效的末端炔烃均偶联催化剂。这种多相催化剂提供了一种非常简单（没有添加配体）和方便的二炔合成，包括碳水化合物衍生物。已经观察到沸石孔径的强烈影响，用具有大内部笼的沸石获得高（定量）产率。沸石酸性位点在反应中的作用已被指出。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200800848
• 作为产物：
  描述：

  D-GlcNAc 在 硫酸 、 silica gel 作用下， 反应 2.0h， 生成 propargyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation

  摘要：

  Fischer glycosylation, a widely used technique for the preparation of simple alkyl or aryl glycosides, has a few drawbacks including the use of strong mineral acids, excess alcohols, high temperature and long reaction times. This manuscript highlights a modification using sulfuric acid immobilized on silica as catalyst for the preparation of glycosides from free sugars such as D-glucose, D-galactose, D-mannose, L-rhamnose, L-fucose, N-acetyl-D-glucosamine and D-maltose with a diverse range of alcohols to afford a series of useful sugar derivatives in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.165

文献信息

• Novel Glycoconjugate of 8-Fluoro Norfloxacin Derivatives as Gentamicin-resistant<i>Staphylococcus aureus</i>Inhibitors: Synthesis and Molecular Modelling Studies
  作者：Chandra S. Azad、Shome S. Bhunia、Atul Krishna、Praveen K. Shukla、Anil K. Saxena

  DOI：10.1111/cbdd.12503

  日期：2015.10

  resistance Staphylococcus aureus. Among these compounds, the compound 10g showed better antibacterial activity (MIC = 3.12 μg/ml) than gentamicin (Escherichia coli (12.5 μg/ml), Staphylococcus aureus (6.25 μg/ml) and Klebsiella pneumonia (6.25 μg/ml), including gentamicin resistant (>50 μg/ml) strain in vitro). The docking studies suggest DNA gyrase of Staphylococcus aureus as a probable target for the

  由于抗生素耐药性致病生物的高流行，抗生素耐药性已成为临床实践中的关注主题。鉴于较小阻力的流行在属于氨基糖苷类的抗生素化合物即。美国食品药品监督管理局（FDA）批准的庆大霉素用于治疗葡萄球菌感染，在临床分离的金黄色葡萄球菌中也有耐药性，这是一系列通过使用铜（I）具有高区域选择性的新型8氟诺氟沙星类似物的新型糖缀合物。合成了1-O-炔丙基单糖催化1、3-偶极环加成并评估了其对庆大霉素耐药性金黄色葡萄球菌的抗菌活性。在这些化合物中，化合物10克显示出更好的抗菌活性（MIC = 3.12  μ微克/毫升）比庆大霉素（大肠杆菌（12.5  μ微克/毫升），金黄色葡萄球菌（6.25  μ克/ ml）和肺炎克雷伯菌（6.25  μ克/毫升），包括庆大霉素抗性（> 50  μ克/ ml）的菌株在体外）。对接研究表明，金黄色葡萄球菌的DNA促旋酶可能是化合物10g的抗菌作用的靶标。
• Synthesis of novel triazole-derived glycopeptides as analogs of α-dystroglycan mucins
  作者：Marcelo Fiori Marchiori、Giulia Pompolo Iossi、Leandro Oliveira Bortot、Marcelo Dias-Baruffi、Vanessa Leiria Campo

  DOI：10.1016/j.carres.2018.11.004

  日期：2019.1

  followed by hydrogenation reactions. Subsequently, glycopeptides 3 (23%) and 4 (12%) were obtained by solid phase synthesis, involving sequential couplings of Fmoc-protected amino acids or the glycosyl amino acids 1 and 2, followed by cleavage from resin, N-acetylation and O-deacetylation (NaOMe) reactions. Lastly, enzymatic galactosylation of glycopeptide 3 with bovine β-1,4-GalT showed that it was not

  α-Dystroglycan（α-DG）粘蛋白对于维持肌纤维的结构和功能稳定性至关重要，并且在糖基化程度低时，它们直接参与病理过程，例如营养不良性糖病。因此，这项工作报告了新的1,2,3-三唑衍生的糖基氨基酸αGlcNAc-1-O-三唑-2Manα-ThrOH（1）和Gal-β1,4-αGlcNAc-1-O-三唑的合成-2Manα-ThrOH（2），然后固相组装得到相应的糖肽NHAcThrVal [αGlcNAc-1-triazol-2Manα] ThrIleArgGlyOH（3）和NHAcThrVal [Gal-β1,4-αGlcNAc-1-triazol-2Manα] ThrIleArgGlyOH（4）作为α-DG粘蛋白的类似物。铜（I）辅助合成1（72％）和2（35％）的糖基氨基酸1，叠氮化物-糖基氨基酸αManN3-FmocThrOBn（5）与相应的炔烃官能化糖2'-丙炔基-αGl
• Direct Glycosylation of Unprotected and Unactivated Sugars Using Bismuth Nitrate Pentahydrate
  作者：Innaiah K. Polanki、Siva H. Kurma、Asish K. Bhattacharya

  DOI：10.1080/07328303.2015.1028585

  日期：2015.5.4

  Bi(NO3)(3), a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high alpha-selectivity. Further, an expedient separation of alpha- and beta-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.
• Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists
  作者：Vishal Kumar Rajput、Hakon Leffler、Ulf J. Nilsson、Balaram Mukhopadhyay

  DOI：10.1016/j.bmcl.2014.05.063

  日期：2014.8

  A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4 N, -4C, -7, -8 N, -9 N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8 N, and 9 N with up to 40-fold affinity enhancements relative to methyl alpha-D-galactopyranoside due to the coumarylmethyl moieties. (C) 2014 Elsevier Ltd. All rights reserved.
• ‘Click chemistry’ in CuI-zeolites: a convenient access to glycoconjugates
  作者：Aurélien Alix、Stefan Chassaing、Patrick Pale、Jean Sommer

  DOI：10.1016/j.tet.2008.06.086

  日期：2008.9

  Zeolites modified with Cu-I ions are efficient catalyst for 'click' reactions involving carbohydrates and aminoacid derivatives. Glycopeptides and oligosaccharides mimics as well as multivalent carbohydrate derivatives have been obtained in good to high yield using heterogeneous Cu-I-modified zeolite catalysts. Contrarily to expectation, pore sizes and internal shapes within zeolites were not a limitation and large glucosyl ditriazoles, disaccharide triazoles, and glucosylated triazolylaminoacids could easily be obtained. Such Cu-I-zeolite heterogeneous catalysts greatly facilitated products recovery, through an easy filtration-solvent evaporation sequence, thus offering a convenient alternative to current methods. (C) 2008 Elsevier Ltd. All rights reserved.