Mono-6-Substituted Cyclodextrins—Synthesis and Applications

Kasal, Petr; Jindřich, Jindřich

doi:10.3390/molecules26165065

Cited by 11 publications

(11 citation statements)

References 245 publications

(293 reference statements)

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“…Methanesulfonylation rarely results in monosulfonyl esters due to the small and reactive species. The bulkier tosyl group seems more appropriate for monosubstitution [ 114 ], but the reaction shows a strong solvent effect [ 111 , 115 , 116 , 117 ]. Although mesitylene- [ 118 , 119 ] and naphthylsulfonyl [ 120 ] esters are also suitable leaving groups, their production costs are higher and the regioselectivity of the reagents used is minimal [ 120 , 121 , 122 ].…”

Section: Discussionmentioning

confidence: 99%

“…Sulfonyl ester CDs are good intermediates, but the replacement of the sulfonyl group to the most common azido function or a heteroatom, like S [ 114 ] or Se [ 131 ], shows a solvent effect. Hydrolysis occurs in water [ 132 ] and N , N -dimethyl substitution occurs in DMF [ 133 ], while in DMSO, oxidation [ 134 ] can occur that reduces the yield, and, many times, the byproducts are hard to remove.…”

Section: Discussionmentioning

confidence: 99%

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Comparison of the Conventional and Mechanochemical Syntheses of Cyclodextrin Derivatives

et al. 2023

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Many scientists are working hard to find green alternatives to classical synthetic methods. Today, state-of-the-art ultrasonic and grinding techniques already drive the production of organic compounds on an industrial scale. The physicochemical and chemical behavior of cyclodextrins often differs from the typical properties of classic organic compounds and carbohydrates. The usually poor solubility and complexing properties of cyclodextrins can require special techniques. By eliminating or reducing the amount of solvent needed, green alternatives can reform classical synthetic methods, making them attractive for environmentally friendly production and the circular economy. The lack of energy-intensive synthetic and purification steps could transform currently inefficient processes into feasible methods. Mechanochemical reaction mechanisms are generally different from normal solution-chemistry mechanisms. The absence of a solvent and the presence of very high local temperatures for microseconds facilitate the synthesis of cyclodextrin derivatives that are impossible or difficult to produce under classical solution-chemistry conditions. Although mechanochemistry does not provide a general solution to all problems, several good examples show that this new technology can open up efficient synthetic pathways.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Comparison of the Conventional and Mechanochemical Syntheses of Cyclodextrin Derivatives

et al. 2023

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“…After proper purification, the yield of the desired product 2 was around 25%. Readers can also find more information on problematic p-toluenesulfonylation, subsequent azidation and reduction, in a recently published review [5].…”

Section: Batch Synthesis Of 6 a -O-(p-toluenesulfonyl)β-cd (Ts-β-cd 2)mentioning

confidence: 99%

“…From the synthetic point of view, the most important derivatives are those versatile intermediates that can be effectively transformed according to the requirements of the specific application. The modification of a monosubstituted CD with a suitable functional group is an easier process than the optimization of a new monosubstitution reaction on a native CD [5].…”

Section: Introductionmentioning

confidence: 99%

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

Orosz¹,

Ujj²,

Kasal³

et al. 2023

Beilstein J. Org. Chem.

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The first continuous flow method was developed for the synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin starting from native β-cyclodextrin through three reaction steps, such as monotosylation, azidation and reduction. All reaction steps were studied separately and optimized under continuous flow conditions. After the optimization, the reaction steps were coupled in a semi-continuous flow system, since a solvent exchange had to be performed after the tosylation. However, the azidation and the reduction steps were compatible to be coupled in one flow system obtaining 6-monoamino-6-monodeoxy-β-cyclodextrin in a high yield. Our flow method developed is safer and faster than the batch approaches.

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“…Mono-6-(4-methylbenzenesulfonyl)-β-CD is the most important precursor to further functionalize the primary hydroxyl groups (C-6) of β-CD, since 4methylbenzenesulfonylate is a good leaving group and can be easily substituted by other nucleophiles [5][6]. The most convenient procedure to prepare mono-6-(4methylbenzenesulfonyl)-β-CD is by using 4methylbenzenesulfonyl imidazole as an important reagent reacting with β-CD in a basic medium [7].…”

Section: ■ Introductionmentioning

confidence: 99%

Phase Transfer Catalyzed Preparation of 4-Methylbenzenesulfonyl Imidazole for Regioselective Synthesis of Mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin

Muderawan

Mudianta²,

Giri³

2022

Indones. J. Chem.

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The preparation of 4-methylbenzenesulfonyl imidazole by using triethylamine as an effective phase‐transfer catalyst (PTC) under mild biphasic conditions has been studied intensively. The method can be used for large-scale preparation with high purity and high yield of 4-methylbenzene-sulfonyl imidazole. The result in 4-methylbenzenesulfonyl imidazole has been successfully applied for the regioselective synthesis of mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin in an aqueous medium. This synthetic methodology concept, together with the synthetic versatility of PTC, provides a general and reliable general strategy for the practical and industrial regioselective synthesis of highly valuable mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin as a key intermediate for the single functional isomer mono-substituted cyclodextrin derivatives. As characterized by FTIR, NMR and mass spectrometry, mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin was obtained in high purity.

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Mono-6-Substituted Cyclodextrins—Synthesis and Applications

Cited by 11 publications

References 245 publications

Comparison of the Conventional and Mechanochemical Syntheses of Cyclodextrin Derivatives

Comparison of the Conventional and Mechanochemical Syntheses of Cyclodextrin Derivatives

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

Phase Transfer Catalyzed Preparation of 4-Methylbenzenesulfonyl Imidazole for Regioselective Synthesis of Mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin

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