A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection

• Stefanie Wolfram,
• Hendryk Würfel,
• Stefanie H. Habenicht,
• Christine Lembke,
• Phillipp Richter,
• Eckhard Birckner,
• Rainer Beckert and
• Georg Pohnert

Beilstein J. Org. Chem. 2014, 10, 2470–2479, doi:10.3762/bjoc.10.258

• BPT (1). BPT (1) is thus transformed efficiently in the CuAAC reaction and the products such as 11 can be detected with high sensitivity using LC–MS. Besides the coupling product of BPT (11) only the low fluorescent 14 shows unique isotopic patterns caused by the two isotopes 79Br and 81Br. This

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

• Silvia Bernardi,
• Paola Fezzardi,
• Gabriele Rispoli,
• Stefania E. Sestito,
• Francesco Peri,
• Francesco Sansone and
• Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

• Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy 10.3762/bjoc.10.175 Abstract Four novel calix[4]arene-based glycoclusters were synthesized by conjugating the saccharide units to the macrocyclic scaffold using the CuAAC reaction and using long and hydrophilic ethylene glycol spacers

• intramolecular CuAAC reaction with an adjacent azido-arm [37]. Firstly, we decided to evaluate the effectiveness of the two approaches dipolarophile-on-the-calix and dipolarophile-on-the-sugar by using a galactose and cone calixarene scaffolds. This investigation was carried out with the idea to extend the study

• convergent synthetic approach. This approach was based on the connection, by CuAAC reaction, of the azido-terminating tetraacetylgalactose 5 [40][41] to calix[4]arene 8 decorated at the upper rim with alkyne terminating chains (Scheme 1). In order to introduce the alkyne units at the upper rim of the

The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and

• that enabled a late-stage, modular addition of the hydrocarbon chains; the products of which could be taken straight into the high-throughput CuAAC reaction. To this end, diol 2 was synthesised by esterification of commercially available 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid (1), according

• , as well as placing the alkyne a further methylene unit from the very bulky tertiary centre, which may have hindered the CuAAC reaction. Using the above methods, a total of twenty tails were synthesised (11 double and 9 triple-chained, Table 1). These consisted of saturated chains with systematic

Microwave-assisted Cu(I)-catalyzed, three-component synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles

• Yogesh Kumar,
• Vijay Bahadur,
• Anil K. Singh,
• Virinder S. Parmar,
• Erik V. Van der Eycken and
• Brajendra K. Singh

Beilstein J. Org. Chem. 2014, 10, 1413–1420, doi:10.3762/bjoc.10.145

• first, followed by the formation of triazole by CuAAC reaction to give the desired product 4a. Conclusion We developed a novel microwave-assisted, Cu(I)-catalyzed, three-component reaction for the synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles in good to

Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

• Mathieu L. Lepage,
• Alessandra Meli,
• Anne Bodlenner,
• Céline Tarnus,
• Francesco De Riccardis,
• Irene Izzo and
• Philippe Compain

Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

• microwave-assisted CuAAC reaction (Scheme 2). The multiconjugation reaction proceeded smoothly to afford the six desired DNJ clusters 9 in 69–95% yields. With the exception of octavalent iminosugars 9c (n = 6) and 9d (n = 9), these compounds showed complex 1H NMR spectra at room temperature as exemplified

Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM₃-lactone mimetic

• Renato Ribeiro-Viana,
• Elena Bonechi,
• Javier Rojo,
• Clara Ballerini,
• Giuseppina Comito,
• Barbara Richichi and
• Cristina Nativi

Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

• functionalized with an alkyne group by a Cu(I) azide–alkyne cycloaddition (CuAAC) reaction. Then, the mimetic 6 with a butyne group at the anomeric position, which is required for the conjugation to the glycodendron 7 (Scheme 1), was also prepared as already reported [33]. The synthesis of the tricyclic spiro

• purification the resulting syrup was conjugated with the glycodendron 7 by a CuAAC reaction with CuSO4 as a copper source, sodium ascorbate to reduce Cu(II) to Cu(I) in situ, and tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) to stabilize Cu(I). The solution was treated with a resin (Quadrasil MP) to

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• in contrast to the regularly used precatalyst reagent mixtures is twofold: on the one hand, the characteristics of molecularly defined, well soluble catalysts can be tuned according to the particular requirements of the experiment; on the other hand, the understanding of the CuAAC reaction mechanism

• Huisgen’s azide–alkyne cycloaddition (CuAAC reaction). In fact, the catalytic effect of copper ions had first been mentioned by L’Abbé in 1984 [7], but had henceforth been overlooked until Meldal presented a copper(I)-catalyzed solid-phase synthesis of 1,2,3-triazoles. In this procedure, the terminal alkyne

• copper in the oxidation state +I [8][12][19]. CuAAC catalysis with copper(0) precatalysts The CuAAC reaction proceeds in the presence of coiled copper metal turnings at room temperature by in situ oxidation to copper(I) species [12][13], even though this route takes longer for completion (12–48 hours

End-labeled amino terminated monotelechelic glycopolymers generated by ROMP and Cu(I)-catalyzed azide–alkyne cycloaddition

• Ronald Okoth and
• Amit Basu

Beilstein J. Org. Chem. 2013, 9, 608–612, doi:10.3762/bjoc.9.66

• -defined glycopolymers and enables subsequent polymer terminus functionalization upon deprotection of the Teoc moiety. The polymer 9 can be functionalized with a variety of groups on the side-chain given the generality of the CuAAC reaction, and should be of utility for the synthesis of a variety of

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• of this nature. It was also shown that the three-unit spacer 13 could be used in a one-pot desilylation and CuAAC reaction to give 24, which was found to be fully soluble in water, despite the more lipophilic nature of the active ligand. This finding paves the way for the synthesis and evaluation of

A ferrocene redox-active triazolium macrocycle that binds and senses chloride

• Nicholas G. White and
• Paul D. Beer

Beilstein J. Org. Chem. 2012, 8, 246–252, doi:10.3762/bjoc.8.25

• investigate its anion binding and electrochemical-sensing properties. Results and Discussion Synthesis The CuAAC reaction of ferrocene bis(azide) 1 [12], with a large excess of 1,6-heptadiyne afforded 2 in 50% yield. An intramolecular Eglinton cyclisation reaction was used to prepare the ferrocene bis

Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline

• Xacobe C. Cambeiro,
• Rafael Martín-Rapún,
• Pedro O. Miranda,
• Sonia Sayalero,
• Esther Alza,
• Patricia Llanes and
• Miquel A. Pericàs

Beilstein J. Org. Chem. 2011, 7, 1486–1493, doi:10.3762/bjoc.7.172

• aldehydes. Results and Discussion The preparation of the immobilized catalysts 1a and 1b was easily achieved by a modification of the reported procedure [41][42][43], with the tris(triazolyl)methyl copper complex 3 [76] as the catalyst for the CuAAC reaction between azidomethylpolystyrene, prepared from a

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• –alkyne cycloaddition (CuAAC) reaction [33][34]. Results and Discussion Since their introduction by Palcic and co-workers [35], hydrophobic alkyl glycosides have proven to be valuable derivatives for enzymatic assays, as their lipophilic nature allows easy product isolation by either reversed-phase