110237-97-3

Upstream product

• 123826-46-0 octadeca-O-benzyl-α-Man-(1->4)-<α-Man-(1->4)>4-α-Man-1->SMe 
• 110237-96-2 C₁₆₂H₁₆₉FO₃₀ 
• 100-39-0 benzyl bromide 
• 10016-20-3 alpha cyclodextrin 
• 100-44-7 benzyl chloride 
• 115435-62-6 cyclo<->4)-O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-<(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)>5-(1-)> 
• 134241-82-0 phenyl 2^I,3^I,6^I,2^II,3^II,6^II,2^III,3^III,6^III,2^IV,3^IV,6^IV,2^V,3^V,6^V,2^VI,3^VI,6^VI-octadeca-O-benzyl-1^I-thio-β-maltohexaoside 

Downstream Products

• 10016-20-3 alpha cyclodextrin 

Relevant academic research and scientific papers

Cyclodextrins containing an acetone bridge. Synthesis and study as epoxidation catalysts

Three cyclodextrine derivatives (6A,6 D-di-O-(prop-2-one-1,3-dienyl)-α-cyclodextrin (1), 6-O-(prop-2-one-1-yl)-α-cyclodextrin (2) and 6A,6 D-di-O-(prop-2-one-l, 3-dienyl)-β-cyclodextrin (3)) were synthesised and investigated as epoxidation catalysts. The three compounds were synthesised from the corresponding perbenzylated cyclodextrins which were mono- or didebenzylated in the 6-position using Sinay's method. Reaction with NaH and methallyl chloride in the case of 2, or methallyl dichloride in the case of 1 and 3, followed by dihydroxylation, periodate cleavage and protection group removal gave the target compounds. All three compounds catalysed, in the presence of oxone, the epoxidation of a series of alkenes. Epoxidation was compared to the reaction catalysed by simple ketones and inhibition was studied.

Direct and Regioselective Di-α-fucosylation on the Secondary Rim of β-Cyclodextrin

A straightforward glycosylation method is described to regio- and stereoselectively introduce two α-l-fucose moieties directly to the secondary rim of β-cyclodextrin. Using NMR and MS fragmentation studies, the nonasaccharide structure was determined, which was also visualized using molecular dynamics simulations. The reported glycosylation method proved to be robust on gram-scale, and may be generally applied to directly glycosylate β-cyclodextrins to make well-defined multivalent glycoclusters.

Cyclodextrin tetraplexes: First syntheses and potential as cross-linking agent

The first syntheses of two cyclic tetramers of cyclodextrins, dubbed tetraplexes, are described as well as the use of one of them to form a supramolecular assembly with a modified biopolymer.

Can Hetero-Polysubstituted Cyclodextrins be Considered as Inherently Chiral Concave Molecules?

(Figure Presented) Learning curve: Regioselective twofold deprotection of benzylated cyclodextrins with diisobutylaluminum hydride affords products that can behave as enantiomers. For example, they can act as ligands for enantioselective Pd°-catalyzed reactions and their complexes display opposite circular dichroism signals (see picture). They can thus be seen as being inherently chiral cycle surrogates.

Control of the regioselectivity for new fluorinated amphiphilic cyclodextrins: Synthesis of di- and tetra(6-deoxy-6-alkylthio)- and 6-(perfluoroalkypropanethio)-α-cyclodextrin derivatives

(Figure Presented) Twelve new di- and tetraderivatized α-cyclodextrin molecules having either alkylthio and perfluoroalkylpropanethio functions at the primary face have been synthesized by using the procedure of Sinay for di-O-debenzylation of perbenzylated α-cyclodextrins. A new strategy of protection/deprotection has been developed for introducing the lipophilic chains. The coupling reaction involves the reaction between the appropriate α-cyclodextin derivative, regioselectively modified at C-6 positions by a good leaving group (O-mesityl for disubstituted or iodine for tetrasubstituted derivatives), with the thioalkyl or the thioperfluoroakylpropane chains. These nucleophilic reagents are obtained from the in situ basic hydrolysis of the alkylisothiouronium bromides or perfluoalkylropropane and the isothiouronium iodides. These multistep reactions give the desired amphiphilic α-cyclodextrins in good overall yields of 33% to 58%.

New cup-shaped α-cyclodextrin derivatives and a study of their catalytic properties in oxidation reactions

A series of new α-cyclodextrin derivatives with a substituted propylene bridge attached to the 6-O's of the A,D-glucose units are reported. The compounds were prepared from the known 6A,6D-di-O-(prop-2-methylidene-1,3-dienyl)-hexadeca-O-benzyl-α-cyclodextrin, which was transformed into 6A,6D-di-O-(prop-2-methyl-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-formyl-2-hydroxy-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-aminomethyl-2-hydroxy-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-hydroxymethylidene-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-formyl-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-carboxy-1,3-dienyl)-α-cyclodextrin and 6A,6D-di-O-(prop-2-methoxycarbonyl-1,3-dienyl)-α-cyclodextrin. The new compounds were evaluated for their ability to affect amine and alcohol oxidations in the presence of hydrogen peroxide.

Precise Rate Control of Pseudorotaxane Dethreading by pH-Responsive Selectively Functionalized Cyclodextrins

A family of cyclodextrins functionalized with zero, one, two, or six amines was shown to control the rate of their threading and dethreading on a molecular axle depending on the pH and their substitution pattern. The originality of this system lies in the rate control of the switch by operating the stimulus directly on the macrocycle.

Smart regioselectivity towards mono 6-hydroxyl α-cyclodextrin amphiphilic derivatives

Following the trend of eco-friendly development, a smart regioselective modification is described herein, for mono 6-hydroxyl and penta-alkyl coexistence on the primary face of α-cyclodextrins with no additional catalysis or no enzyme process, just via the adjustment of the ratio of alkali to alkylation agent, with good yields. The novel procedure minimized the tedious protection, deprotection steps and provided useful intermediates for further cutting edge research. Thus, the scope of green and economical access is extended from penta-pentenyl substitution to C4-C6 alkyl group substitution. It was speculated that the mechanism might be controlled by the concentration of alkali in the system and the steric effects of the electrophilic reagent RBr.

Zinc and Copper Complexes of Methylated Di- and Tetraaminocyclodextrins

The α- and β-cyclodextrins with two dimethylamino groups or two trimethylethylenediamino groups attached to the primary face were synthesized and their pKa values were determined by potentiometric titration. The complexation of the four cyclodextrin analogues with zinc and copper was studied by NMR and showed one or two cyclodextrins bound to the metal. Inclusion of 4-halophenols in the metal complexes were also studied.

Hyper-crosslinked cyclodextrin porous polymer: An efficient CO2 capturing material with tunable porosity

We designed and synthesized cyclodextrin (CD)-based hyper-crosslinked porous polymers (HCPPs) for selective CO2 adsorption and storage. We also explored the effect of monomer size on micropore formation, and determined a feasible way to tailor