5,11,17,23-tetrakis(3-azidopropyl)-25,26,27,28-tetrapropoxycalix[4]arene | 913254-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetrakis(3-azidopropyl)-25,26,27,28-tetrapropoxycalix[4]arene
• 英文别名: 5,11,17,23-Tetrakis(3-azidopropyl)-25,26,27,28-tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
• CAS: 913254-44-1
• 化学式: C₅₂H₆₈N₁₂O₄
• 分子量: 925.19
• InChiKey: PZSXTAMTUUHJKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  68
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  94.4
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(3-azidopropyl)-25,26,27,28-tetrapropoxycalix[4]arene 、 3,7-脱水-1,2-二脱氧-4,5,6,8-四-O-(苯基甲基)-D-甘油型-D-古洛-辛-1-炔糖醇 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以63%的产率得到5,11,17,23-tetrakis{3-[4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]propyl}-25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  通过1,2,3-三唑接头在杯[4]芳烃，金刚烷和苯骨架上的C-糖苷簇集

  摘要：

  通过铜（I）催化的叠氮化物与炔烃的经典Huisgen 1,3-偶极环加成反应的现代版本，已经为制备三唑糖簇库铺平了道路。通过适当多官能化的杯[4]芳烃，金刚烷和苯衍生物与乙炔基和叠氮甲基C-的多次环加成，在各种支架上最多构建四个带有碳连接糖基片段的1,4-二取代的1,2,3-三唑环。糖苷。每次环加成反应都具有很高的区域选择性，从而以非常高的收率只产生1，4-二取代的三唑环，其平均收率高达98％。这种方法的高效率及其广泛的范围构成了将各种糖单元连接到多官能化底物上的简单实用方法。

  DOI：

  10.1021/jo0607156
• 作为产物：
  描述：

  5,11,17,23-tetrakis(3-hydroxypropyl)-25,26,27,28-tetrapropoxy-calix[4]arene 在 sodium azide 、 二苯基膦叠氮化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以89%的产率得到5,11,17,23-tetrakis(3-azidopropyl)-25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  通过1,2,3-三唑接头在杯[4]芳烃，金刚烷和苯骨架上的C-糖苷簇集

  摘要：

  通过铜（I）催化的叠氮化物与炔烃的经典Huisgen 1,3-偶极环加成反应的现代版本，已经为制备三唑糖簇库铺平了道路。通过适当多官能化的杯[4]芳烃，金刚烷和苯衍生物与乙炔基和叠氮甲基C-的多次环加成，在各种支架上最多构建四个带有碳连接糖基片段的1,4-二取代的1,2,3-三唑环。糖苷。每次环加成反应都具有很高的区域选择性，从而以非常高的收率只产生1，4-二取代的三唑环，其平均收率高达98％。这种方法的高效率及其广泛的范围构成了将各种糖单元连接到多官能化底物上的简单实用方法。

  DOI：

  10.1021/jo0607156

文献信息

• Copper(I)-Catalyzed Azide-Alkyne Cycloadditions in Ionic Liquids under Amine-Free Conditions
  作者：Alberto Marra、Alessandro Dondoni、Alessandra Vecchi、Angela Chambery、Cinzia Chiappe

  DOI：10.1055/s-0029-1218760

  日期：2010.6

  Copper(I) iodide catalyzed cycloadditions of various combinations of structurally diverse organic azides and terminal alkynes were carried out in a commercially available, polyoxygenated ionic liquid (AMMOENG 100™) without addition of free amine. Unlike the previously tested ionic liquids, this solvent led exclusively to the 1,4-disubstituted triazole regioisomer. alkynes - azides - carbohydrates -

  在不添加游离胺的情况下，在市售的多氧化离子液体（AMMOENG 100™）中进行结构多样的有机叠氮化物和末端炔烃的各种组合的碘化亚铜（I）催化的环加成反应。与先前测试过的离子液体不同，该溶剂仅产生1,4-二取代的三唑区域异构体。 炔烃-叠氮化物-碳水化合物-铜-环加成
• Synthesis of sialoclusters appended to calix[4]arene platforms via multiple azide-alkyne cycloaddition. New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses
  作者：Alberto Marra、Lisa Moni、Daniele Pazzi、Alfredo Corallini、Deborah Bridi、Alessandro Dondoni

  DOI：10.1039/b800598b

  日期：——

  Tetra- and octavalent sialoside clusters were prepared in good yields exploiting for the first time the multiple copper-catalyzed cycloaddition of a propargyl thiosialoside with calix[4]arene polyazides. The cycloadducts featured the hydrolytically stable carbon-sulfur bond at the anomeric position and the 1,4-disubstituted triazole ring as the spacer between the sialic acid moieties and the platform. It was demonstrated that these unnatural motifs did not hamper the desired biological activity of the sialoclusters. In fact, they were able to inhibit, at submillimolar concentrations, the hemagglutination and the viral infectivity mediated both by BK and influenza A viruses.

  通过首次利用丙炔基硫代糖苷与钙[4]炔多氮化物的多重铜催化环加成反应，制备出了四价和八价的硫代糖苷簇，并获得了良好的收率。这些环加成物的特点是在同分异构位上具有水解稳定的碳硫键，而 1,4-二取代的三唑环则是硅杂羧酸分子与平台之间的间隔。研究表明，这些非天然结构并不妨碍硅脂环的预期生物活性。事实上，在亚摩尔浓度下，它们能够抑制 BK 病毒和甲型流感病毒介导的血凝和病毒传染性。
• Microwave-Enhanced Ionothermal CuAAC for the Synthesis of Glycoclusters on a Calix[4]arene Platform
  作者：Alessandra Vecchi、Bernardo Melai、Alberto Marra、Cinzia Chiappe、Alessandro Dondoni

  DOI：10.1021/jo800954z

  日期：2008.8.1

  i-Pr2EtN in three different ionic liquids, that is, [C8dabco][N(CN)2], [C8dabco][Br], and Ammoeng 110. Reactions were performed at 80 °C by thermal and MW dielectric heating. In all cases, multiple cycloadditions took place to give a triazole-linked tetra-C-galactosyl-calix[4]arene in up to 90% yield. The [C8dabco][N(CN)2] ionic liquid was also used to perform the multiclick reactions with propargyl

  四-叠氮基杯[4]芳烃衍生物被允许与乙炔基四反应ö苄基Ç中的CuI的存在和半乳糖苷我-Pr 2将EtN [C在三个不同的离子液体，即，8 DABCO] [N（CN）2 ]，[C 8 dabco] [Br]和Ammoeng110。反应是通过热和MW介电加热在80°C进行的。在所有的情况下，多个环加成发生，得到三唑连接的四Ç半乳糖杯[4]中高达90％的产率芳烃。[C 8 dabco] [N（CN）2 ]离子液体也用于与炔丙基O-乳糖苷和S-唾液甙。
• Synthesis and glycosidase inhibition properties of triazole-linked calixarene–iminosugar clusters
  作者：Alberto Marra、Renaud Zelli、Giuseppe D'Orazio、Barbara La Ferla、Alessandro Dondoni

  DOI：10.1016/j.tet.2014.10.035

  日期：2014.12

  Calixarene iminosugar derivatives bearing four 1-deoxynojirimycin units at the upper or lower rim of calix[4]arenes in a fixed cone conformation were synthesized by copper-catalyzed azide-alkyne cyclo-addition (CuAAC) and their inhibitory activity was evaluated against five glycosidases. Modest but significant affinity enhancements of up to seven per 1-deoxynojirimycin unit over the monovalent iminosugar derivative were observed for the inhibition of Jack bean (Canavalia ensiformis) alpha-mannosidase. It was also demonstrated that the residual copper ions did not contribute to the inhibitory properties of the newly prepared calixarene-based multivalent iminosugars. (C) 2014 Elsevier Ltd. All rights reserved.
• <i>C</i>-Glycoside Clustering on Calix[4]arene, Adamantane, and Benzene Scaffolds through 1,2,3-Triazole Linkers
  作者：Alessandro Dondoni、Alberto Marra

  DOI：10.1021/jo0607156

  日期：2006.9.1

  A route has been paved toward the preparation of triazole glycocluster libraries via the copper(I)-catalyzed modern version of the classical Huisgen 1,3-dipolar cycloaddition of azides to alkynes. Up to four 1,4-disubstituted 1,2,3-triazole rings bearing carbon-linked glycosyl fragments were constructed on various scaffolds via multiple cycloadditions of suitably polyfunctionalized calix[4]arene, adamantane

  通过铜（I）催化的叠氮化物与炔烃的经典Huisgen 1,3-偶极环加成反应的现代版本，已经为制备三唑糖簇库铺平了道路。通过适当多官能化的杯[4]芳烃，金刚烷和苯衍生物与乙炔基和叠氮甲基C-的多次环加成，在各种支架上最多构建四个带有碳连接糖基片段的1,4-二取代的1,2,3-三唑环。糖苷。每次环加成反应都具有很高的区域选择性，从而以非常高的收率只产生1，4-二取代的三唑环，其平均收率高达98％。这种方法的高效率及其广泛的范围构成了将各种糖单元连接到多官能化底物上的简单实用方法。