Efficient preparation of β-<scp>d</scp>-glucosyl and β-<scp>d</scp>-mannosyl ureas and other N-glucosides in carbohydrate melts

Ruß, Carolin; Ilgen, Florian; Reil, Christian; Luff, Claudia; Begli, Alireza Haji; König, Burkhard

doi:10.1039/c0gc00468e

Cited by 30 publications

(8 citation statements)

References 32 publications

(23 reference statements)

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“…Occasional use of silica as a grinding auxiliary was found beneficial for amines in a liquid state. Melting conditions can instead be exploited for the synthesis of N-glycosyl ureas, where the use of acidic catalysts was found beneficial for improved yields [87,88]. Interestingly, an excellent anomeric selectivity was observed when pyranoside products were obtained [87].…”

Section: Other Solvent-free Condensation Reactions On Free Carbohydratesmentioning

confidence: 99%

“…Melting conditions can instead be exploited for the synthesis of N-glycosyl ureas, where the use of acidic catalysts was found beneficial for improved yields [87,88]. Interestingly, an excellent anomeric selectivity was observed when pyranoside products were obtained [87]. Another interesting reaction is the synthesis of sugar dithioacetals catalyzed by bromodimethylsulfonium bromide (Me 2 SBr)Br, easily obtained by reaction of dimethylsulfide with bromine [89].…”

Section: Other Solvent-free Condensation Reactions On Free Carbohydratesmentioning

confidence: 99%

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Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity

et al. 2020

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Owing to their abundance in biomass and availability at a low cost, carbohydrates are very useful precursors for products of interest in a broad range of scientific applications. For example, they can be either converted into basic chemicals or used as chiral precursors for the synthesis of potentially bioactive molecules, even including nonsaccharide targets; in addition, there is also a broad interest toward the potential of synthetic sugar-containing structures in the field of functional materials. Synthetic elaboration of carbohydrates, in both the selective modification of functional groups and the assembly of oligomeric structures, is not trivial and often entails experimentally demanding approaches practiced by specialized groups. Over the last years, a large number of solvent-free synthetic methods have appeared in the literature, often being endowed with several advantages such as greenness, experimental simplicity, and a larger scope than analogous reactions in solution. Most of these methods are catalytically promoted, and the catalyst often plays a key role in the selectivity associated with the process. This review aims to describe the significant recent contributions in the solvent-free synthetic chemistry of carbohydrates, devoting a special critical focus on both the mechanistic role of the catalysts employed and the differences evidenced so far with corresponding methods in solution.

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Section: Other Solvent-free Condensation Reactions On Free Carbohydratesmentioning

confidence: 99%

Section: Other Solvent-free Condensation Reactions On Free Carbohydratesmentioning

confidence: 99%

Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity

et al. 2020

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“…Furthermore, the presence of an acidic catalyst in water can lead to rehydration and condensation of DMF, resulting in unwanted by-products. [166] The DES can even fulfil a triple role as reactant, solvent, and catalyst. As catalysts, para-toluenesulfonic acid and CrCl 2 , were applied, depending on the saccharide used.…”

Section: Application In Organic Synthesismentioning

confidence: 99%

“…As catalysts, para-toluenesulfonic acid and CrCl 2 , were applied, depending on the saccharide used. [166] acid and dimethylurea (3:7), which was applied in the synthesis of hydantoins, [167] dihydropyrimidinones, [168] and pyrimidopyrimidinediones [169] (Scheme 36). Remarkably, in case of sucrose and inulin, hydrolysis into the monosaccharides and dehydration occurred simultaneously in one step.…”

Section: Application In Organic Synthesismentioning

confidence: 99%

Organic Synthesis without Conventional Solvents

Obst

König

2018

Eur J Org Chem

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Organic synthesis without an organic solvent is still the exception. In this microreview, we discuss and compare different synthetic methods that proceed in the absence of conventional organic solvents. This includes solvent‐free methods in solids (mechanochemistry and solid‐state photochemistry), and in neat liquids (thermal and photocatalytic), as well as the application of unconventional solvents, such as ionic liquids and deep‐eutectic solvents. The different approaches are briefly introduced and examples illustrate their specific advantages, followed by a critical discussion of their limitations. Some methods have the intrinsic benefits of solvent‐free operation, such as avoiding solubility problems and side‐reactions with the solvent. However, every method has specific advantages and the demand of the synthetic application is crucial for selecting the best technique.

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“…Organic syntheses, [22][23][24][25][26][27][28] separation processes, [29][30][31][32] biomass processing, [33][34][35][36][37][38] and carbon dioxide adsorption [39,40] constitute the principal fields in which DESs have been applied. Moreover, the eco-friendly and low-toxic character of some DESs has allowed their use as solvents for both natural and synthetic membrane-like structures [41] and proteins, [42,43] and even for microorganism [44] with preservation of their intrinsic activity.…”

Section: Introductionmentioning

confidence: 99%

Deep Eutectic Solvents in Polymerizations: A Greener Alternative to Conventional Syntheses

et al. 2013

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The use of deep eutectic solvents (DESs) that act as all‐in‐one solvent–template–reactant systems offers an interesting green alternative to conventional syntheses in materials science. This Review aims to provide a comprehensive overview to emphasize the similarities and discrepancies between DES‐assisted and conventional syntheses and rationalize certain green features that are common for the three DES‐assisted syntheses described herein: one case of radical polymerization and two cases of polycondensations. For instance, DESs contain the precursor itself and some additional components that either provide certain functionality (e.g., drug delivery and controlled release, or electrical conductivity) to the resulting materials or direct their formation with a particular structure (e.g., hierarchical‐type). Moreover, DESs provide a reaction medium, so polymerizations are ultimately carried out in a solventless fashion. This means that DES‐assisted syntheses match green chemistry principles 2 and 5 because of the economy of reagents and solvents, whereas the functionality incorporated by the second component allows the need for any post‐synthesis derivatization to be minimized or even fully avoided (principle 8). DESs also provide new precursors that favor more efficient polymerization (principle 6) by decreasing the energy input required for reaction progress. Finally, the use of mild reaction conditions in combination with the compositional versatility of DESs, which allows low‐toxic components to be selected, is also of interest from the viewpoint of green chemistry because it opens up the way to design biocompatible and/or eco‐friendly synthetic methods (principle 3).

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Efficient preparation of β-d-glucosyl and β-d-mannosyl ureas and other N-glucosides in carbohydrate melts

Cited by 30 publications

References 32 publications

Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity

Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity

Organic Synthesis without Conventional Solvents

Deep Eutectic Solvents in Polymerizations: A Greener Alternative to Conventional Syntheses

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