Efficient microwave-assisted synthetic protocols and in silico behaviour prediction of per-substituted β-cyclodextrins

Martina, Katia; Cravotto, Giancarlo; Caporaso, Marina; Rinaldi, Laura; Villalonga-Barber, C.; Ermondi, Giuseppe

doi:10.1039/c3ob40909k

Cited by 6 publications

(3 citation statements)

References 28 publications

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“…These include a lack of unpleasant reagents, such as thiolacetate(s) and sodium sulfide, and the absence of disulfide formation during the reaction. Although the thiuronium method for the preparation of thiol derivatives of CDs is known, − the use of DMF, large excess of TU (usually 10 molar fold), high temperature, and long classic synthesis reaction time naturally result in side reactions, such as the formation of the 3 I ,6 I -anhydroglucopyranose or N,N -dimethylamino unit.…”

Section: Results and Discussionmentioning

confidence: 99%

Nucleophilic Substitutions of 6^I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill

Jicsinszky

Caporaso

Tuza³

et al. 2016

ACS Sustainable Chem. Eng.

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The tosyl group (Ts) on 6 I-O-(p-toluenesulfonyl)--cyclodextrin has been substituted with halogenides, nitrogen and sulfur nucleophiles under mechanochemical conditions and the reaction has been investigated in this work. The preparation of mono-substituted cyclodextrin (CD) derivatives, such as azido-, thioureido-, iodo-and thioethers, is shown to be more advantageous in a planetary ball mill (BM) than classic solution methods. All BM reactions

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Section: Results and Discussionmentioning

confidence: 99%

Nucleophilic Substitutions of 6^I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill

Jicsinszky

Caporaso

Tuza³

et al. 2016

ACS Sustainable Chem. Eng.

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“…MW irradiation efficiently afforded pure products. A series of amino derivatives were obtained by displacement of heptakis(6-deoxy-6-iodo)-β-CD (MW reactor 150 W) at 85 °C for 1 h (yield range 52–69%) [ 52 ]. Analogously catalytic hydrogenation in a pressure-resistant MW reactor, gave heptakis(6-amino-6-deoxy)-β-CD from a solution of heptakis(6-azido-6-deoxy)-β-CD in methanol/H 2 O [ 53 ].…”

Section: Reviewmentioning

confidence: 99%

Enabling technologies and green processes in cyclodextrin chemistry

Cravotto¹,

Caporaso²,

Jicsinszky³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe design of efficient synthetic green strategies for the selective modification of cyclodextrins (CDs) is still a challenging task. Outstanding results have been achieved in recent years by means of so-called enabling technologies, such as microwaves, ultrasound and ball mills, that have become irreplaceable tools in the synthesis of CD derivatives. Several examples of sonochemical selective modification of native α-, β- and γ-CDs have been reported including heterogeneous phase Pd- and Cu-catalysed hydrogenations and couplings. Microwave irradiation has emerged as the technique of choice for the production of highly substituted CD derivatives, CD grafted materials and polymers. Mechanochemical methods have successfully furnished greener, solvent-free syntheses and efficient complexation, while flow microreactors may well improve the repeatability and optimization of critical synthetic protocols.

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“…The different strategies envisaged to carry out the opening reaction of the epoxide obtained by CDs is described. Indeed, activation modes such as ultrasound [8,9], microwaves [10,11], or mechanochemistry [12] are considered as useful green tools for the chemical modification of cyclodextrins. Cravotto et al reported some works where ball milling is used to obtain well-known CD derivatives but under green and solventless conditions and with better yields [13,14].…”

Section: Introductionmentioning

confidence: 99%

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

et al. 2020

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Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected.

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Efficient microwave-assisted synthetic protocols and in silico behaviour prediction of per-substituted β-cyclodextrins

Cited by 6 publications

References 28 publications

Nucleophilic Substitutions of 6^I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill

Nucleophilic Substitutions of 6^I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill

Enabling technologies and green processes in cyclodextrin chemistry

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

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Efficient microwave-assisted synthetic protocols and in silico behaviour prediction of per-substituted β-cyclodextrins

Cited by 6 publications

References 28 publications

Nucleophilic Substitutions of 6I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill

Nucleophilic Substitutions of 6I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill

Enabling technologies and green processes in cyclodextrin chemistry

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

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Product

Resources

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Nucleophilic Substitutions of 6^I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill

Nucleophilic Substitutions of 6^I-O-Monotosyl-β-cyclodextrin in a Planetary Ball Mill