(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide | 219584-28-8

• 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-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide
• 英文别名: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide；2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranosyl azide；2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-azido-3-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 219584-28-8
• 化学式: C₃₈H₅₁N₃O₂₅
• 分子量: 949.828
• InChiKey: XJHZQAJAJCFLSM-KPOMAQCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  66
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  324
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide 在 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-1-N-phenyl acetyl-α-D-glucopyranosylamine
  参考文献：
  名称：

  Stereoselective Synthesis of α- and β-Glycosylamide Derivatives from Glycopyranosyl Azides via Isoxazoline Intermediates

  摘要：

  Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure of the phosphorimine. Coupling of in situ generated isoxazolines with acylating reagents gave mixtures of alpha- or beta-glycopyranosyl amides. The alpha/beta ratio depended upon the acylating reagent and metal salts employed. For example, coupling of isoxazoline 3 with Z-Asp-(SPy)-OBn in the presence of CuCl2 gave exclusively alpha-N-glucopyranosylasparagine derivative 8. This general procedure has been applied to mono-, di-, and trisaccharide systems.

  DOI：

  10.1021/ja028694u
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-bromide 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  “Click chemistry”en route to pseudo-starch

  摘要：

  使用“点击化学”实现了淀粉片段类似物的快速组装。具体来说，使用 Cu(I) 催化的叠氮糖的 [3 + 2] 偶极环加成反应合成了两种十六糖模拟物，其中包含通过 [1,2,3]-三唑连接到麦芽糖核心的两条平行的麦芽七糖基链和 6,6−2 - 和 4α,6α-二炔丙基化对甲氧基苯基麦芽糖苷。

  DOI：

  10.1039/b504293c

文献信息

• Iron(iii) chloride as an efficient catalyst for stereoselective synthesis of glycosyl azides and a cocatalyst with Cu(0) for the subsequent click chemistry
  作者：Santosh B. Salunke、N. Seshu Babu、Chien-Tien Chen

  DOI：10.1039/c1cc13370e

  日期：——

  A highly efficient and mild method for azido glycosylation of glycosyl β-peracetates to 1,2-trans glycosyl azides was developed by using inexpensive FeCl3 as the catalyst. In addition, we demonstrated, for the first time, that FeCl3 in combination with copper powder can promote 1,3-dipolar cycloaddition (click chemistry) of azido glycosides with terminal alkynes. Good to excellent yields were obtained with exclusive formation of a single isomer in both glycosyl azidation and subsequent cycloaddition processes.

  一种高效而温和的方法被开发出来，利用廉价的FeCl3作为催化剂，实现了糖基β-过乙酸酯的叠氮糖基化反应，制备了1,2-反式糖基叠氮化合物。此外，我们首次证明了FeCl3与铜粉的组合能够促进叠氮糖基与末端炔烃的1,3-偶极环加成反应（点击化学）。在糖基叠氮化和随后的环加成反应过程中，均获得了良好至优异的产率，并且仅形成单一的异构体。
• [EN] NOVEL SULFATED OLIGOSACCHARIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'OLIGOSACCHARIDES SULFATÉS
  申请人：PROGEN PHARMACEUTICALS LTD

  公开号：WO2009049370A1

  公开（公告）日：2009-04-23

  The invention relates to novel compounds that have utility as inhibitors of heparan sulfate-binding proteins; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment of a mammalian subject.

  这项发明涉及具有作为肝素硫酸结合蛋白抑制剂的效用的新化合物；包含这些化合物的组合物；以及利用这些化合物和组合物对哺乳动物主体进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗的用途。
• AuBr₃-catalyzed azidation of per-<i>O</i>-acetylated and per-<i>O</i>-benzoylated sugars
  作者：Jayashree Rajput、Srinivas Hotha、Madhuri Vangala

  DOI：10.3762/bjoc.14.56

  日期：——

  Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr₃ in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1–3 h at room temperature, the per-O-benzoylated disaccharides needed 2–3 h of heating at 55 °C.

  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。
• Design, synthesis of oleanolic acid-saccharide conjugates using click chemistry methodology and study of their anti-influenza activity
  作者：Yangqing Su、Lingkuan Meng、Jiaqi Sun、Weijia Li、Liang Shao、Kexuan Chen、Demin Zhou、Fan Yang、Fei Yu

  DOI：10.1016/j.ejmech.2019.111622

  日期：2019.11

  (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor. Herein, as a further study, we report the preparation of a series of OA-saccharide conjugates via the CuAAC reaction, and the anti-influenza activity of these compounds was evaluated in vitro. Among them, compound 11b, an OA-glucose conjugate, showed a significantly increased anti-influenza activity with an IC50 of 5.47 μM, and no

  进入抑制剂的开发是抑制流感病毒的新兴方法。在我们之前的研究中，齐墩果酸（OA）被发现是一种轻度的流感血凝素（HA）抑制剂。在本文中，作为进一步的研究，我们报道了通过CuAAC反应制备一系列OA-糖缀合物的方法，并在体外评估了这些化合物的抗流感活性。其中，OA-葡萄糖偶联物化合物11b显示出显着提高的抗流感活性，IC50为5.47μM，在100μM下未观察到对MDCK细胞的明显细胞毒性作用。血凝抑制试验和对接实验表明11b可能通过作用于HA蛋白而干扰流感病毒的感染。广谱抗流感实验显示11b对5种不同菌株具有强大的效力，包括甲型和乙型流感病毒，IC50值处于低微摩尔水平。总体而言，该发现进一步扩展了OA-糖缀合物在抗流感病毒药物设计中的用途。
• Fullerene glycoconjugates: A general synthetic approach via cycloaddition of per-O-acetyl glycosyl azides to [60]fullerene
  作者：Arihiro Yashiro、Yoshihiro Nishida、Masatomi Ohno、Shoji Eguchi、Kazukiyo Kobayashi

  DOI：10.1016/s0040-4039(98)02047-4

  日期：1998.12

  A general synthetic way to incorporate oligosaccharides into [60]fullerene via cycloadditon and deacetylation is presented. The cycloaddition reaction in refluxing chlorobenzene gave a mixture of two unseparable stereoisomers of N-β-glycopyranosyl [5,6]-azafulleroids in 13∼28% yields for per-O-acetyl glycosyl azide of d-glucopyranose, d-galactopyranose, lactose, maltose, and maltotriose.

  提出了通过环己二酮和脱乙酰基将寡糖掺入[60]富勒烯的一般合成方法。在回流的氯苯中进行环加成反应，得到两种不可分离的N -β-甘露糖基[5,6]-氮杂富勒烯类立体异构体的混合物，d-吡喃葡萄糖，d-吡喃半乳糖，乳糖的过O-乙酰基糖基叠氮化物的产率为13％至28％。，麦芽糖和麦芽三糖。