94789-63-6

Upstream product

• 94789-61-4 6-monohydroxy permethylated β-cyclodextrin 
• 98-59-9 p-toluenesulfonyl chloride 
• 67217-55-4 mono-6-deoxy-6-(p-tolylsulphonyl)-β-cyclodextrin 
• 74-88-4 methyl iodide 
• 166305-90-4 heptakis(2,3-di-O-methyl)-6^I-O-p-tolylsulfonyl-cyclomaltoheptaose 
• 333-27-7 methyl trifluoromethanesulfonate 

Downstream Products

• 1253122-32-5 6A-deoxy-6A-diphenylphosphinyl-2A,2B,2C,2D,2E,2F,2G,3A,3B,3C,3D,3E,3F,3G,6B,6C,6D,6E,6F,6G-eicosa-O-methyl-β-cyclodextrin 
• 1313515-41-1 6(A)-O-[4-(diphenylphosphino)phenyl]-2(A),2(B),2(C),2(D),2(E),2(F),2(G),3(B),3(C),3(D),3(E),3(F),3(G),6(B),6(C),6(D),6(E),6(F),6(G)-eicosa-O-methyl-β-cyclodextrin 

Relevant academic research and scientific papers

Preparation and photodynamic activities of silicon(IV) phthalocyanines substituted with permethylated β-cyclodextrins

A series of silicon(IV) phthalocyanines linked to two permethylated β-cyclodextrin moieties through different spacers at the axial positions have been synthesized and characterized. The effects of these spacers on the photophysical properties and in vitro photodynamic activities have also been examined. Having two bulky hydrophilic substituents, all of these compounds are soluble and essentially nonaggregated in DMF and even in aqueous media. The fluorescence and singlet oxygen quantum yields in DMF are lower for the analogue with the shortest separation between the amino group in the spacer and the phthalocyanine ring. The fluorescence quantum yield of this compound increases in water probably due to protonation of the amino group, which inhibits the reductive quenching process. This series of compounds also exhibit photocytotoxicity toward HT29 human colon adenocarcinoma and HepG2 human hepatocarcinoma cells with IC50 values in the range of 0.04-1.32 μM. The analogue with an α,ω-aminohydroxypentyl linker shows the highest potency, which can be ascribed to its high cellular uptake and high efficiency in generating intracellular reactive oxygen species. This compound also shows preferential localization in the lysosome, induces cell death mainly through apoptosis, and inhibits the growth of tumor in vivo. The results suggest that it is a promising photosensitizer for photodynamic therapy. Copyright

Convenient synthesis of mono(6A-N-allylamino-6 A-deoxy)permethylated β-cyclodextrin: A promising chiral selector for an HPLC chiral stationary phase

Mono(6-(p-toluenesulfonyl))permethylated β-cyclodextrin, a versatile precursor for a wide variety of mono-functionalized permethyl β-cyclodextrins, has been generated successfully by the direct methylation of monotosylated cyclodextrin. This afforded a convenient synthesis of mono(6A-N-allylamino-6A-deoxy)permethylated β-cyclodextrin. Hydrosilylation of the chiral selector with (EtO) 3SiH and reaction of the resultant reactive siloxane with pristine silica gel afforded a facile entry into a structurally well-defined chiral HPLC stationary phase.

An N-heterocyclic carbene ligand based on a β-cyclodextrin-imidazolium salt: Synthesis, characterization of organometallic complexes and Suzuki coupling

A new ligand based on permethylated β-cyclodextrin bearing a methylimidazole group was synthesized. In the presence of this N-heterocyclic carbene ligand, silver or palladium complexes were generated. Interestingly, palladium species based on this ligand

Sustainable Gold Catalysis in Water Using Cyclodextrin-tagged NHC-Gold Complexes

The synthesis of 10 water-soluble β-cyclodextrin-tagged NHC-gold(I) complexes is described. Key steps are nucleophilic substitutions, as well as, copper-(CuAAC)- and ruthenium-(RuAAC)-catalyzed azide alkyne cycloadditions. Whereas the CuAAC reliably affor

A manganese porphyrin-α-cyclodextrin conjugate as an artificial enzyme for the catalytic epoxidation of polybutadiene

We describe a manganese porphyrin-α-cyclodextrin conjugate as a catalyst for the epoxidation of cis-polybutadiene with trans-epoxide preference, which is a reverse stereoselectivity as compared to normal porphyrin catalysts. A clamp-like mechanism is prop

Synthesis, rhodium complexes and catalytic applications of a new water-soluble triphenylphosphane-modified β-cyclodextrin

A new triphenylphosphane based on a β-cyclodextrin skeleton (PM-β-CD-OTPP) was synthesized. This ligand can be dispersed in water by using the nanoprecipitation method. Transmission electron microscopy and NMR spectroscopy showed that PM-β-CD-OTPP is aggregated in water and forms a stable dispersion. Its aqueous solubility can be dramatically increased in the presence of selected water-soluble guests by formation of inclusion complexes. Associated to a rhodium precursor, PM-β-CD-OTPP is able to generate soluble rhodium species in water. In addition, NMR experiments showed that the cyclodextrin cavity remains accessible for a guest even when PM-β-CD-OTPP is coordinated to rhodium. Finally, this ligand was efficient for rhodium-catalyzed hydrogenation and hydroformylation performed in aqueous medium.

New phosphane based on a β-cyclodextrin, exhibiting a solvent-tunable conformation, and its catalytic properties

A new diphenylphosphane based on a β-cyclodextrin skeleton that exhibits a dual solubility in water and in organic solvent was synthesised. Interestingly, a solvent-dependent conformation change was evidenced by NMR spectroscopy studies; the self-inclusion of a phenyl group of the phosphane moiety into cyclodextrin cavity observed in water disappeared in organic solvents due to a change in conformation. Hydrogenation or hydroformylation reactions performed in water and in organic solvents showed that this ligand was able to stabilise catalytically active rhodium species in solution. In the case of the hydroformylation reaction, it was demonstrated that regioselectivity was influenced by the solventdependent conformation of the ligand.

Acetylenic cyclodextrins for multireceptor architectures: Cups with sticky ends for the formation of extension wires and junctions

A mono-6-O-propargyl permethylated β-cyclodextrin, 3, has been prepared by two synthetic routes as a versatile building block for the construction of cyclodextrin dimers and trimers with a core junction which is potentially electron conducting. Glaser-Hay

Convenient scaffold for forming heteroporphyrin arrays in aqueous media

A new methodology for preparing heteroporphyrin arrays in aqueous solution has been presented. The present method is based on the extremely strong ability of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMe-β-CD) to include 5,10,15,20-tetrakis(p-substitut

New large-scale preparations of versatile 6-O-monotosyl and 6-monohydroxy permethylated α-, β-, and γ-cyclodextrins

New practical methods for preparation of versatile 6-O-monotosyl and 6-monohydroxy permethylated α-, β-, and γ-cyclodextrins are described.