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Upstream product

• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 106-93-4 ethylene dibromide 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 74-95-3 1,1-dibromomethane 
• 99070-23-2 4-(2-bromo-ethoxy)-3-methoxy-benzaldehyde 
• 121-33-5 vanillin 

Downstream Products

• 81329-97-7 [3-methyloxy-4-(2-iodoethoxy)phenyl]methanol 
• 347894-40-0 2-{[4-(2-bromoethoxy)-3-methoxybenzyl]-oxy}tetrahydro-2H-pyran 
• 161910-66-3 C₉₉H₁₂₆O₁₅ 
• 98757-24-5 2,7,12-tris<2-(4-hydroxymethyl-2-methoxyphenoxy)ethoxy>-3,8,13-trimetoxy-10,15-dihydro-5H-tribenzocyclononene 
• 347894-45-5 2,7,12-Trimethoxy-3,8,13-tris{2-[2-methoxy-4-(tetrahydropyran-2-yloxymethyl)phenoxy]ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclonenene 
• 347894-43-3 2-[4-(2-iodoethoxy)-3-methoxybenzyloxy]-tetrahydropyran 

Relevant academic research and scientific papers

Hemicryptophane-assisted electron transfer: A structural and electronic study

Three copper(ii)@hemicryptophane complexes with various cavity sizes and shapes, Cu(ii)@1, Cu(ii)@2 and Cu(ii)@3, were synthesized and characterized by near-IR/vis and EPR spectroscopies. The spectroscopic data are consistent with the presence of a trigonal-bipyramidal geometry of the N4Cu· H2O core, in accord with the energy-minimized structures obtained from DFT calculations. Cyclic voltammetry studies in CH2Cl 2 showed irreversible redox processes, whereas electrolysis coulometry indicated that Cu(ii)/Cu(i) complexes could be interconverted. Electrochemistry data of the complexes stress the crucial role of the cage structure of the hemicryptophane in the thermodynamics of the electron transfer. The Royal Society of Chemistry 2013.

Azaphosphatrane organocatalysts in confined space: Cage effect in CO 2 conversion

The endohedral functionalization of a molecular cage by an azaphosphatrane unit has allowed for the creation of highly engineered catalytic cavities for efficient conversion of CO2 into cyclic carbonates. Strong structure/activity/stability correlations have been demonstrated by careful adjustment of the size, shape, and electronic properties of the hemicryptophane host.

Cyclotriveratrylene-BINOL-Based Host Compounds: Synthesis, Absolute Configuration Assignment, and Recognition Properties

New host compounds combining a cyclotriveratrylene (CTV) unit and three binaphthol moieties have been synthesized enantiomerically and diastereomerically pure. The use of a chemical correlation allows for the assignment of their absolute configuration. The energy barrier of epimerization was measured, suggesting that no intramolecular hydrogen bonding occurs between the hydroxyl groups of the binaphthols. These open-shell host compounds were then tested in the recognition of carbohydrates; a preferential binding of mannose toward glucose was observed, and good diastereoselectivities were reached (up to 1:10). This recognition of sugar derivatives by open-shell CTV-based host compounds is unprecedented and opens up the way for a wider use of this easily accessible class of molecules as chiral sensors.

Design, synthesis, in silico and in vitro studies for new nitric oxide‐releasing indomethacin derivatives with 1,3,4‐oxadiazole‐2‐thiol scaffold

Starting from indomethacin (IND), one of the most prescribed non‐steroidal anti‐inflammatory drugs (NSAIDs), new nitric oxide‐releasing indomethacin derivatives with 1,3,4‐oxadiazole‐ 2‐thiol scaffold (NO‐IND‐OXDs, 8a‐p) have been developed as a safer and

Enantio- A nd Substrate-Selective Recognition of Chiral Neurotransmitters with C3-Symmetric Switchable Receptors

We report on the synthesis of C3-symmetric enantiopure cage molecules 1, which exhibit remarkable to exclusive enantioselective recognition properties toward chiral ammonium neurotransmitters. Strong changes in the substrate selectivity are als

Enantiopure encaged Verkade's superbases: Synthesis, chiroptical properties, and use as chiral derivatizing agent

Verkade's superbases, entrapped in the cavity of enantiopure hemicryptophane cages, have been synthesized with enantiomeric excess (ee) superior to 98%. Their absolute configuration has been determined by using electronic circular dichroism (ECD) spectros

High-relaxivity Gd(III)-hemicryptophane complex

The polytopic hemicryptophane cage HC1 combining a cyclotriveratrylene (CTV) unit and a tris(2-aminoethyl)amine (tren) moiety connected by three 2-hydroxyisophthalamide linkers was synthesized in 12 steps. The resulting highly functionalized covalent host

Large-Scale Synthesis of Enantiopure Molecular Cages: Chiroptical and Recognition Properties

A convenient and efficient gram-scale synthesis for enantiopure hemicryptophane-tren (tren=tris(2-aminoethyl)amine) derivatives has been developed. The four-step synthesis is based on the optical resolution of a key intermediate, cyclotriveratrylene, for

A "Smart" 129Xe NMR biosensor for pH-dependent cell labeling

Here we present a "smart" xenon-129 NMR biosensor that undergoes a peptide conformational change and labels cells in acidic environments. To a cryptophane host molecule with high Xe affinity, we conjugated a 30mer EALA-repeat peptide that is α-helical at pH 5.5 and disordered at pH 7.5. The 129Xe NMR chemical shift at room temperature was strongly pH-dependent (Δδ = 3.4 ppm): δ = 64.2 ppm at pH 7.5 vs δ = 67.6 ppm at pH 5.5, where Trp(peptide)-cryptophane interactions were evidenced by Trp fluorescence quenching. Using hyper-CEST NMR, we probed peptidocryptophane detection limits at low-picomolar (10-11 M) concentration, which compares favorably to other NMR pH reporters at 10-2-10-3 M. Finally, in biosensor-HeLa cell solutions, peptide-cell membrane insertion at pH 5.5 generated a 13.4 ppm downfield cryptophane-129Xe NMR chemical shift relative to pH 7.5 studies. This highlights new uses for 129Xe as an ultrasensitive probe of peptide structure and function, along with potential applications for pH-dependent cell labeling in cancer diagnosis and treatment.

Synthesis and physico-chemical properties of the first water soluble Cu(ii)@hemicryptophane complex

A hemicryptophane ligand soluble in water at neutral pH was obtained thanks to the derivatization of the cyclotribenzylene unit with three carboxylate groups. The corresponding Cu(ii) complex was then synthesized and its spectroscopic and electrochemical