2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranosyl azide | 106192-56-7

• 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-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranosyl azide
• 英文别名: 2,3,4-Tri-O-acetyl-6-azido-6-desoxy-β-D-glucopyranosylazid；per-O-acetyl-6-azido-6-deoxy-β-D-glucopyranosyl azide；2,3,4-tri-O-acetyl-1,6-diazido-β-D-glucose；2,3,4-Tri-O-acetyl-1,6-diazido-1,6-dideoxy-beta-D-glucopyranoside min.；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-azido-2-(azidomethyl)oxan-3-yl] acetate
• CAS: 106192-56-7
• 化学式: C₁₂H₁₆N₆O₇
• 分子量: 356.295
• InChiKey: NXPXGFMQQOVNCD-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranosyl azide 在 benzyltriethylammonium tetrathiomolybdate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到2,3,4-tri-O-acetyl-1-amino-6-azido-1,6-dideoxy-β-D-glucose
  参考文献：
  名称：

  用四硫代钼酸酯将异头叠氮化物选择性还原为胺：β-D-糖基胺的合成。

  摘要：

  许多β-d-糖基叠氮化物衍生物在用四硫代钼酸盐处理后进行还原，以仅在非常温和和中性的反应条件下不发生异构化的情况下产生相应的β-d-糖基胺。在反应条件下，乙酰基，烯丙基，苯甲酰基和苄基保护基保持不变。观察到异头叠氮化物还原的排他选择性，而C-2和C-6叠氮化物保持不变。

  DOI：

  10.1021/jo0266947
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 在 叠氮化锂 、 叠氮基三甲基硅烷 、 四氯化锡 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Gyoergydeak, Zoltan; Szilagyi, Laszlo, Liebigs Annalen der Chemie, 1987, p. 235 - 242

  摘要：

  DOI：

文献信息

• Synthesis of Multivalent Glycoclusters from 1-Thio-β-<scp>d</scp>-galactose and Their Inhibitory Activity against the β-Galactosidase from <i>E. coli</i>
  作者：Alejandro J. Cagnoni、Oscar Varela、Sébastien G. Gouin、José Kovensky、María Laura Uhrig

  DOI：10.1021/jo102421e

  日期：2011.5.6

  to 4 residues of 1-thio-β-d-galactose. The yields went from moderate to excellent, depending on the valency of the desired product. Deacetylation with Et3N/MeOH/H2O led to the final products. Complete characterization of the products was performed by NMR spectroscopy and HR-MS techniques. Their activities as inhibitors of β-galactosidase from E. coli were determined by using the Lineweaver−Burk method

  据报道，旨在与生物系统相容的多价糖簇的合成。已经合成了各种通过可变长度的低聚乙二醇链连接至末端三键的1-硫代-β- d-半乳糖苷。另外，通过用NaN 3 / PPh 3 / CBr 4直接叠氮化由海藻糖，麦芽糖和麦芽三糖制备含叠氮化物的寡糖支架。硫代半乳糖苷残基和叠氮化物支架之间在微波辐射下的点击反应提供了含有1-4个1-硫代-β- d-半乳糖残基的糖簇家族。取决于所需产品的化合价，收率从中等提高到极好。用Et脱乙酰3 N / MeOH / H 2 O生成最终产物。通过NMR光谱和HR-MS技术对产物进行完全表征。通过使用Lineweaver-Burk方法确定了它们作为大肠杆菌β-半乳糖苷酶抑制剂的活性。使用亲水性碳水化合物支架合成多价半乳糖苷代表了一种改善其药代动力学和生物利用度的有趣方法。另外，硫糖苷键的存在将改善它们在生物流体中的稳定性。
• Metabolic labeling and molecular enhancement of biological materials using bioorthogonal reactions
  申请人：The General Hospital Corporation

  公开号：US20170362266A1

  公开（公告）日：2017-12-21

  The present application provides methods of functionalizing an organ or tissue of a mammal by administering a nutrient (e.g., peracetylated N-azido galactosamine Ac4GalNAz) to the mammal or by culturing an organ or tissue in a bioreactor containing such nutrient. The present application also provides methods of selectively functionalizing extracellular matrix (ECM) of an organ or tissue of a mammal by administering a nutrient (e.g., peracetylated N-azido galactosamine Ac4GalNAz) to the mammal. In some aspects, the present application provides a decellularized scaffold of a mammalian organ or tissue comprising an extracellular matrix, wherein the extracellular matrix of the decellularized scaffold is functionalized with a chemical group that is reactive in a bioorthogonal chemical reaction, such as an azide chemical group. The present application also provides biological prosthetic mesh and mammalian organs and tissues for transplantation prepared according to the methods of the application.

  本申请提供了一种通过向哺乳动物投与营养物质（例如，乙酰化N-叠氮基半乳糖氨酸Ac4GalNAz）或在含有这种营养物质的生物反应器中培养器官或组织来功能化哺乳动物器官或组织的方法。本申请还提供了一种通过向哺乳动物投与营养物质（例如，乙酰化N-叠氮基半乳糖氨酸Ac4GalNAz）来选择性地功能化哺乳动物器官或组织的细胞外基质（ECM）的方法。在某些方面，本申请提供了哺乳动物器官或组织的脱细胞支架，其中脱细胞支架的细胞外基质被功能化为在生物正交化学反应中具有反应性的化学基团，例如叠氮基团。本申请还提供了根据本申请的方法制备的生物义肢网和哺乳动物器官和组织用于移植。
• Synthesis of new saccharide azacrown cryptands
  作者：Michalina Pintal、Florence Charbonniere-Dumarcay、Alain Marsura、Stanisław Porwański

  DOI：10.1016/j.carres.2015.07.007

  日期：2015.9

  New cryptands including bis-azacrown and saccharidic moieties in their structure were prepared in several steps by applying Staudinger-aza-Wittig reaction (SAW). Syntheses have been started from cheap, easily available commercial compounds such as D-glucose, D-cellobiose and D-lactose subsequently transformed into their derivatives in fairly good yields (60-65%) and suitable to give desired final cryptands by direct SAW coupling reactions. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides
  作者：Katuri J.V. Paul、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2008.08.073

  日期：2008.10

  A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated beta- as well as alpha-D-glycopyranosyl azides, including the 1,6-diazide derived from D-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(beta-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields. (c) 2008 Elsevier Ltd. All rights reserved.
• Direct azidation of unprotected carbohydrates with PPh3/CBr4/NaN3. Modulation of the degree of substitution
  作者：Sébastien G. Gouin、José Kovensky

  DOI：10.1016/j.tetlet.2007.02.092

  日期：2007.4

  We describe herein a modified procedure for the direct and regioselective synthesis of polyazido-sugars, that currently requires multistep syntheses. This protocol allows to modulate the degree of azidation obtained when the reagents to substrate ratio is changed. (c) 2007 Elsevier Ltd. All rights reserved.