2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl azide | 33639-93-9

• 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-benzoyl-β-D-glucopyranosyl azide
• 英文别名: N-Methoxy-N-methyl (1,2,3,4-Di-O-isopropylidene-D-galactopyranose uronic acid) amide；2,3,4,6-tetra-O-benzoyl-beta-d-glucopyranosyl azide；[(2R,3R,4S,5R,6R)-6-azido-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 33639-93-9
• 化学式: C₃₄H₂₇N₃O₉
• 分子量: 621.603
• InChiKey: SHZKMJFYJDZFHE-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl azide 在 吡啶 、 4-二甲氨基吡啶 、 platinum(IV) oxide 、 氢气 、 caesium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.67h， 生成 (2R,3R,4S,5R,6R)-2-acetamido-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides

  摘要：

  The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected beta-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. beta-Glycosyl amides were then prepared in 67% to 81% yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.

  DOI：

  10.1080/07328303.2012.663431
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 gold(III) bromide 、 叠氮基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  AuBr₃-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

  摘要：

  在这里，我们首次报道了对经过O-乙酰化和O-苯甲酰化的糖进行顺式异构体化合成的成功实例，通过使用催化量的亲氧化金Br₃，产率良好至优良。该方法适用于广泛易得的O-乙酰化和O-苯甲酰化糖。虽然与O-乙酰化和O-苯甲酰化的单糖在室温下1-3小时内反应完成，但O-苯甲酰化的二糖需要在55°C下加热2-3小时。

  DOI：

  10.3762/bjoc.14.56

文献信息

• First noscapine glycoconjugates inspired by click chemistry
  作者：Kunj B. Mishra、Ram C. Mishra、Vinod K. Tiwari

  DOI：10.1039/c5ra07321a

  日期：——

  A number of novel 7-O-noscapine glycoconjugates have been synthesized starting from noscapine, an alkaloid found in the opium plant, via two successive steps. The first step is a selective 7-O-demethylation of noscapine and the next is a subsequent propargylation which affords 7-O-propargyl noscapine (3) in good yield. The structure was confirmed by extensive spectroscopic data including single crystal

  已经通过两个连续的步骤，从鸦片植物中发现的一种生物碱-诺斯卡汀开始合成了许多新颖的7- O-诺斯卡汀糖缀合物。第一步是Noscapine的选择性7- O-去甲基化，第二步是随后的炔丙基化，以良好的收率得到7- O-炔丙基基Noscapine（3）。通过包括单晶X射线数据在内的大量光谱数据证实了该结构。研究了发达的Noscapine衍生物3与糖基叠氮化物6a–m的1,3-偶极环加成反应，得到了三唑连接的第二代Noscapine类似物，其糖缀合物形式（8a–m ）以增强Noscapine的治疗功效。
• Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives
  作者：Zuo-Peng Zhang、Ye Zhong、Zhen-Bin Han、Lin Zhou、Hua-Sheng Su、Jian Wang、Yang Liu、Mao-Sheng Cheng

  DOI：10.3390/ijms22115482

  日期：——

  A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

  一系列糖苷修饰的噻二唑磺胺衍生物已通过“尾部方法”设计和合成，并针对碳酸酐酶II、IX和XII的抑制活性进行评估。大多数化合物显示出较高的拓扑极性表面积（TPSA）值和优秀的酶抑制活性。一些化合物对HT-29、MDA-MB-231和MG-63人类癌细胞系的存活率在常氧和低氧条件下进行了检查，它们显示出一定的细胞存活抑制作用。此外，发现这一系列化合物具有提高肿瘤细胞微环境pH值的能力。所有结果证明，糖苷修饰的噻二唑磺胺具有重要的CA IX抑制剂开发研究前景。
• The Reaction of Thio Acids with Azides:  A New Mechanism and New Synthetic Applications
  作者：Ning Shangguan、Sreenivas Katukojvala、Rachel Greenberg、Lawrence J. Williams

  DOI：10.1021/ja0294919

  日期：2003.7.1

  A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides

  提出了一种基于硫代酸和有机叠氮化物反应的基本机理修正的新酰胺合成策略。数据表明在该反应中没有形成胺作为中间体。建议了通过噻三唑啉中间体进行的替代机制。该反应已用于制备使用常规方法难以获得的简单且结构复杂的酰胺。该反应具有化学选择性，对未受保护的底物有效，并与非质子和质子溶剂（包括水）相容。
• Highly efficient and recyclable pre-catalysts based on mono- and dinuclear heteroleptic Cu(I) dithio- PPh3 complexes to produce variety of glycoconjugate triazoles
  作者：Avadhesh K. Singh、Chote Lal Yadav、Kunj Bihari Mishra、Santosh K. Singh、Ajit N. Gupta、Vinod Kumar Tiwari、Michael G.B. Drew、Nanhai Singh

  DOI：10.1016/j.mcat.2019.03.009

  日期：2019.6

  (C, H, N) analysis, IR, UV–vis., 1H, 13C1H}, and 31P1H} NMR spectroscopy and their structures have been revealed by X-ray crystallography. In the structures of (1,2)/(3,4) the copper atoms are situated within a four coordinate (P2S2)/(P2NS) distorted tetrahedral geometry. Notably in the dinuclear complexes 3 and 4, the dithiocarbimate ligands are bonded in a S, S- chelating mode to one copper atom

  高效且可重复使用的预制单核和双核杂多铜（I）二硫代氨基甲酸酯和二硫代氨基甲酸酯络合物基催化剂，[Cu（PPh 3）2（L）]和[ Cu 2（PPh 3）4（L） ]  ñ - （4-甲基吡啶基） - ñ - （3-甲基吡啶基）二硫代氨基甲酸-大号1 1，N-甲基呋喃基-N- methylthiophenedithiocarbamate-大号2 2 ; 4-氯苯dithiocarbimate 2-大号3 3，4-bromobenzenesulfonyldithiocarbimate 2-大号4 4）已被用于叠氮化物和炔烃的环加成反应中，以在Click化学中形成各种糖缀合物三唑。这些新的预催化剂已通过元素（C，H，N）分析，IR，UV-vis。，1 H，13 C 1 H}和31 P 1 H} NMR光谱进行了表征，并且它们的结构已经过由X射线晶体学显示。在（结构1，2）/（3，4）的铜原子位于四个坐标（P内2小号2）/（P
• Synthesis of artemisinin derived glycoconjugates inspired by click chemistry
  作者：Lakshmi Goswami、Sayantan Paul、Tharun K. Kotammagari、Asish K. Bhattacharya

  DOI：10.1039/c8nj05737k

  日期：——

  Herein we describe the synthesis of artemisinin based glycoconjugates (9a–i) through employing a Cu(I)-catalysed reaction between β-propargylated dihydroartemisinin (7a) and azido sugars (8a–i), with moderate to excellent yields. Our synthesized artemisinin based glycoconjugates (9a–i) could prove to be an interesting class of bioactive molecules, suitable for the study of their various biological

  本文中，我们描述了通过使用β-炔丙基二氢青蒿素（7a）和叠氮基糖（8a-i）之间的Cu（I）催化反应以青蒿素为基础的糖缀合物（9a–i）合成，具有中等至极好的收率。我们合成的基于青蒿素的糖缀合物（9a–i）可能被证明是一类有趣的生物活性分子，适用于研究其各种生物活性。