46929-51-5

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 108-73-6 3,5-dihydroxyphenol 

Downstream Products

• 213555-12-5 1,3,5-tris(2-p-toluenesulfonyloethoxy)benzene 
• 864383-29-9 1,3,5-tris-(2-(3-(t-butoxycarbonyl)propylmalonyl)ethoxy)benzene 
• 784213-08-7 1,3,5-tris(2-N-methylaminoethoxy)benzene 
• 213555-13-6 1,3,5-tris[4'-(p-toluenesulfonyl)-1'-oxa-4'-azabutyl]benzene 
• 213555-17-0 C₄₅H₅₁N₃O₁₂S₃ 
• 213555-19-2 C₄₈H₅₇N₃O₁₂S₃ 
• 1000074-83-8 1,3,5-tris((2'-(2''-bromoethyl)malonyl)ethoxy)benzene 
• 1187465-85-5 1,3,5-tris-(2-methylmalonyl)ethoxybenzene 

Relevant academic research and scientific papers

Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates

Described is a tetrabutylammonium fluoride-mediated hydroxyalkylation reaction of phenols with cyclic carbonates. This operationally simple method enables the synthesis of a variety of aryl β-hydroxyethyl ethers in good to excellent yields with a very small amount of catalyst loading (0.1–1 mol%). Of particular note is the efficient conversion of aromatic diols and phloroglucinol to the corresponding bis- and tris-hydroxyethylated products. To further showcase the versatility of this protocol, guaifenesin was prepared with a single step by the condensation of guaiacol and glycerol carbonate. We also developed a flow ethoxylation process permitting the continuous synthesis of multiflorol. (Figure presented.).

A study towards the regioselective synthesis of the e,e,e trisadduct of C60 via the [4+2] Diels-Alder reaction with tethers bearing orthoquinodimethane precursors

The regioselective synthesis of an e,e,e trisadduct of C60 via the Diels-Alder reaction with orthoquinodimethanes has been attempted employing the tether-directed remote functionalization approach. Opened-structure tether 10 and macrocyclic tethers 16 and 21 were synthesized for this purpose. The functionalization of C60 afforded inseparable mixtures of regiomeric trisadducts and the regioselective formation of the e,e,e trisadduct was not feasible even when the more preorganized tethers 16 and 21 were employed. The in situ thermal generation of orthoquinodimethanes from the 1,2-bis(bromomethyl)benzene precursors requires high temperatures and is followed by fast, irreversible cycloaddition with C60 to afford thermally stable products, which prevents the achievement of high regioselectivities.

The first one-pot synthesis of a chiral pentakis-adduct of C60 utilising an opened-structure malonate tether

A pentakis-adduct of C60 with an incomplete octahedral addition pattern was synthesised via a one-pot procedure using a tether equipped with five malonate moieties. The five-fold Bingel cyclopropanation of C60 was completely regiosel

Synthesis of new cores and their use in the preparation of polyester dendrimers

Six dendrimer and dendron cores terminated by hydroxyl groups that are neither phenolic nor cleavable by hydrogenolysis have been prepared in a consistent one-pot manner from terminal allyl groups by reduction of the product of reductive ozonolysis. Some of the terminal allyl derivatives are new and others have been prepared by new methods. The well-known O-benzylidene derivative of 2,2′-bis(hydroxymethyl)propanoic acid was shown to be the cis-stereoisomer. A new AB3-type anhydride, tris(benzyloxymethyl) acetic anhydride has been prepared. It was demonstrated that these cores and dendrons could be assembled into first and second generation homo- and mixed polyester dendrimers.

Synthesis and orthogonal functionalization of [60]fullerene e,e,e-trisadducts with two spherically defined addend zones

e,e,e-Trisadducts 13 and 15 have been prepared by a highly regioselective threefold cyclopropanation of tripodal malonates 10 and 12 with C60. The yield and regioselectivity depend on the length and structure of the tethers that connect the malonate units to the focal benzene core of 13-15. As a consequence of the template-directed synthesis, all ce.e-trisadducts were formed as in/out isomers exclusively and contain two spherically well-defined addend zones with equatorial and polar orientation, respectively. By variation of the outer malonate termini of the tethers, selective functionalization of the equatorial addend zone could be achieved, thus leading to fine-tuning of intermolecular interactions, such as solubility or aggregation phenomena. After removal of the focal benzene moiety in 14 and 15, selective functionalization of the polar addend zone could be achieved. Strong intramolecular hydrogen-bonding networks of the polar substituents in the polar addend zone could be observed by 1H NMR spectroscopic analysis. By orthogonal functionalization of both addend zones, fullerene derivatives 44-48 could be synthesized as one single in/out isomer, thus greatly enhancing the potential of e,e,e-trisadducts as building blocks in supramolecular architectures.

Method of synthesis of water soluble fullerene polyacids using a malonate reactant

In one embodiment, the present invention is directed to a method for synthesizing compounds of the formula where Cm is a fullerene having m carbon atoms, the method comprising the steps of forming a linear malonate compound of the formula where each Z is the same or different and is a straight-chain or branched-chain aliphatic radical having from 1-30 carbon atoms which may be unsubstituted or monosubstituted or polysubstituted by identical or different substitutents, in which radicals up to every third —CH2— unit can be replaced by O or NR″, n is an integer from 2 to 10, and the unfilled valences of the first and nth malonate groups are filled with bonds to hydrogen, a hydrocarbon group or substituted hydrocarbon group having 1-20 carbon atoms, or a chain containing unsubstituted or substituted aryl or other cyclic groups; or (ii) a branched malonate compound of the formula where Z′ is an aliphatic radical having from 1-30 carbon atoms which may be unsubstituted or monosubstituted or polysubstituted by identical or different substitutents, in which radicals up to every third —CH2— unit can be replaced by O or NR″; and n is an integer from 2 to 10; reacting said malonate compound with Cm to form an adduct of the formula each Z is bonded to both one carboxylate group of a first malonate moiety and one carboxylate group of a second malonate moiety and the unfilled valences of the first and nth malonate groups are filled with bonds to hydrogen, a hydrocarbon group or substituted hydrocarbon group having 1-20 carbon atoms, or a chain containing unsubstituted or substituted aryl or other cyclic groups; and hydrolyzing said adduct to form the compound.

Regioselective synthesis and zone selective deprotection of [60]fullerene tris-adducts with an e,e,e addition pattern

D3h-symmetrical tripodal tris(malonate) tethers have been used for the synthesis of [60]fullerene tris-adducts with an e,e,e addition pattern bearing topologically distinct polar and equatorial addend zones that can selectively be deprotected. The Royal Society of Chemistry 2005.

A self-assembled multivalent pseudopolyrotaxane for binding galectin-1

A self-assembled pseudopolyrotaxane consisting of lactoside-displaying cyclodextrin (CD) "beads" threaded onto a linear polyviologen "string" was investigated for its ability to inhibit galectin-1-mediated T-cell agglutination. The CDs of the pseudopolyro

High-affinity, low-molecular-mass displacers for ion-exchange chromatography

A method for separating one or more components of a biomolecule mixture by means of an ion exchange chromatographic system operated in the displacement mode includes sequentially perfusing the system with a first solution including the biomolecule mixture, and a second solution including a displacer having a structure selected from formula I and formula II:

Facile Synthesis of Benzene-bridged Azaoxamacrobicyclic Ligands

Five new barrel-shaped macrobicyclic compounds capable of complexation with anions have been prepared. Intermediate triamines were prepared in one-step using a triple Mitsonobu reaction, thereby shortening the overall synthetic sequence. A previously prepared benzene-bridged hexaazamacrocycle was prepared in only four-steps.