2,3,4,6-tetra-O-benzyl-D-galactopyranosyl azide | 200501-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl azide
• 英文别名: (2R,3R,4S,5S,6R)-2-azido-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 200501-41-3
• 化学式: C₃₄H₃₅N₃O₅
• 分子量: 565.669
• InChiKey: NKVQKPBQIGZTBQ-BWNLSPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactopyranosyl azide 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、150.0 kPa 条件下， 生成 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl amine
  参考文献：
  名称：

  Small molecule glycoconjugates with anticancer activity

  摘要：

  Glycoconjugates are combinations of sugar moieties with organic compounds. Due to their biological resemblance, such structures often have properties that are desirable for drugs. In this study we designed and synthesised several glycoconjugates from small molecular quinolines and substituted gluco- and galactopyranosyl amines. Although the parent quinoline compounds were inactive in affordable concentrations, the glycoconjugates that were obtained appeared to be cytotoxic against cancer cells at the micromolar level. When combined with copper ions, their activity increased even further. Their mechanism of action is connected to the formation of reactive oxygen species and the intercalation of DNA. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.01.061
• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷四乙酸酯 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 生成 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl azide
  参考文献：
  名称：

  Small molecule glycoconjugates with anticancer activity

  摘要：

  Glycoconjugates are combinations of sugar moieties with organic compounds. Due to their biological resemblance, such structures often have properties that are desirable for drugs. In this study we designed and synthesised several glycoconjugates from small molecular quinolines and substituted gluco- and galactopyranosyl amines. Although the parent quinoline compounds were inactive in affordable concentrations, the glycoconjugates that were obtained appeared to be cytotoxic against cancer cells at the micromolar level. When combined with copper ions, their activity increased even further. Their mechanism of action is connected to the formation of reactive oxygen species and the intercalation of DNA. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.01.061

文献信息

• Traceless Staudinger Ligation of Glycosyl Azides with Triaryl Phosphines:  Stereoselective Synthesis of Glycosyl Amides
  作者：Aldo Bianchi、Anna Bernardi

  DOI：10.1021/jo060409s

  日期：2006.6.1

  α-Glycosyl amides can be synthesized from the corresponding O-benzyl-α-glycosyl azides using a traceless Staudinger ligation with diphenylphosphanyl-phenyl esters 4. All the phosphines employed and their phenol precursors are stable to air at 4 °C for months. Fast intramolecular trapping of the reduction intermediates results in the direct formation of the amide link, which, in turn, prevents epimerisation

  α-糖基酰胺可通过无痕施陶丁格与二苯基膦酰基-苯基酯的连接由相应的O-苄基-α-糖基叠氮化物合成4。所用的所有膦及其苯酚前体在4°C的空气中均可保持稳定数月。还原中间体的快速分子内捕集导致酰胺键的直接形成，继而防止了差向异构化并允许在异头碳上保留构型。当反应在极性非质子溶剂中进行时，产率和α-选择性高。苄基醚保护基的去除是通过催化氢化来实现的。α-糖基酰胺代表了一类实际上未开发的不可水解的单糖衍生物，可以作为糖模拟物找到有用的应用。NMR光谱的构象研究证实，葡萄糖，半乳糖和fuco系列中的脱保护α-糖基酰胺保留了单糖的正常吡喃糖构象。膦的反应4用四ø -乙酰基葡糖基叠氮化物是nonstereoconservative，并在良好的产率，并与来自两个α和β叠氮化物开始完整的立体选择性获得β糖基酰胺。
• Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group
  作者：Mukta Shaw、Rima Thakur、Amit Kumar

  DOI：10.1021/acs.joc.8b02422

  日期：2019.1.18

  synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate and noncarbohydrate-based glycosyl acceptors and leads to their corresponding O/N-glycosides in good to excellent yields with regeneration of reusable and easily separable phenylpropiolic acid. Differentially protected PPGs reacted well under the optimized reaction

  使用新合成的台式稳定苯丙酸苯丙酯糖基（PPG）供体，开发了一种有效且操作简单的金（III）催化的糖基化方案。金（III）催化的PPG活化与各种基于碳水化合物和非碳水化合物的糖基受体进行得很好，并导致其相应的O / N-糖苷的收率好至极好，并具有可重复使用和易于分离的苯丙酸的再生。差异保护的PPG在优化的反应条件下反应良好。特别地，在甘露糖基和鼠李糖基PPG供体上观察到良好的异头选择性。初步的机理研究表明，与酯基相邻的三键的存在对于激活至关重要，并且基于PPG的供体显示出比类似的乙酸和苯甲酸酯供体更高的反应性。
• Synthesis of Sugar-Derived Triazole- and Pyridine-Based Metal Complex Ligands
  作者：Thomas Ziegler、Jochen Kraft、Daniel Schmollinger、Jakob Maudrich

  DOI：10.1055/s-0034-1379473

  日期：——

  for metals were prepared by copper-catalyzed coupling (CLICK reaction) of 2-ethynylpridine, 2-ethynyl-5-nitropyridine, 2-ethynylquinoline, and 2,6-diethynylpyridine with 12 protected glycosyl azides in the gluco and galacto series and 2 benzyl azides. The 1,2,3-triazole-linked glycoconjugates prepared were used as ligands for the copper-catalyzed addition of phenylacetylene to N-benzylideneaniline to

  摘要 通过2-乙炔基吡啶，2-乙炔基-5-硝基吡啶，2-乙炔基喹啉和2,6-二乙炔吡啶与十二种保护的糖基叠氮化物的铜催化偶联（CLICK反应），制备了一系列30种金属的双齿和三齿配体在葡萄糖和半乳糖系列中和2个苄基叠氮化物。制备的1,2,3-三唑连接的糖缀合物用作配体，用于铜催化的苯乙炔加成到N-亚苄基苯胺上，得到手性N-（1,3-二苯基丙-2-炔-1-基）苯胺。 通过2-乙炔基吡啶，2-乙炔基-5-硝基吡啶，2-乙炔基喹啉和2,6-二乙炔吡啶与十二种保护的糖基叠氮化物的铜催化偶联（CLICK反应），制备了一系列30种金属的双齿和三齿配体在葡萄糖和半乳糖系列中和2个苄基叠氮化物。制备的1,2,3-三唑连接的糖缀合物用作配体，用于铜催化的苯乙炔加成到N-亚苄基苯胺上，得到手性N-（1,3-二苯基丙-2-炔-1-基）苯胺。
• Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate
  作者：Masanori Mizuno、Takayuki Shioiri、Masanori Mizuno

  DOI：10.1039/a705768g

  日期：——

  The direct stereoselective conversion of various alcohols and hexopyranoses into the corresponding alkyl azides and glycosyl azides, respectively, is efficiently accomplished by using bis(p-nitrophenyl) phosphorazidate and DBU.

  使用双（对硝基苯基）磷酸酰肼和DBU，可以高效地将各种醇和己糖吡喃转化为相应的烷基叠氮化物和糖苷叠氮化物。
• 1,5-Disubstituted 1,2,3-Triazolylation at C1, C2, C3, C4, and C6 of Pyranosides: A Metal-Free Route to Triazolylated Monosaccharides and Triazole-Linked Disaccharides
  作者：Anirban Kayet、Tanmaya Pathak

  DOI：10.1021/jo401576n

  日期：2013.10.4

  prepared from 3-O-methylated- and 3-O-benzylated glucofuranosides as well as 3-O-benzylated allofuranoside were also subjected to 1,3-dipolar cycloaddition reactions with six azidopyranosides under similar reaction conditions to generate a series of 1,5-disubstituted triazole-linked disaccharides. The synthesis of all 1,5-disubstituted triazolylated monosaccharides as well as all 1,5-disubstituted triazole

  使一对易于获得的源自苯乙烯环氧化物和单甲苯基化甘油的乙烯基砜与六个不同的叠氮基吡喃侧核苷反应，这些叠氮基吡喃侧核苷在C1，C2，C3，C4，C6以及与C1连接的胞外链的末端具有叠氮基。该反应主要在高温下在水中进行，没有任何金属催化剂，以高产率提供区域选择性的1，5-二取代的三唑基化吡喃糖苷。由3- O-甲基化的和3- O-苄基化的呋喃呋喃糖苷以及3- O制备的另一组环外乙烯基砜在相似的反应条件下，还将苄基化的富呋喃糖苷与六个叠氮基吡喃糖苷进行1，3-偶极环加成反应，以生成一系列的1，5-二取代的三唑连接的二糖。首次报道了所有1，5-二取代的三唑基化单糖以及所有1，5-二取代的三唑连接的二糖的合成。叠氮基和乙烯基砜基团周围的立体异构体在决定反应的结果中起着重要作用。这种强大而实用的途径具有开发复杂的1,5-二取代的1,2,3-三唑基化碳水化合物的潜力。