Synthesis of benzylidenated hexopyranosides in ionic liquids

Zhang, Jianguo; Ragauskas, Arthur J.

doi:10.1016/j.carres.2005.10.007

Cited by 14 publications

(4 citation statements)

References 40 publications

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Section: Synthesis Of Functionalized Carbohydrates In Ilsmentioning

confidence: 99%

“…The benzylidenation reaction was repeated five times without loss in efficiency. 174 Using acid catalysis, ion-exchange resin, or 4-toluene sulfonic acid, it was possible to obtain 5-hydroxyfurfural and 2,5disusbtituted furanic derivatives by dehydration of fructose. This reaction was studied in DMSO, ILs 175 The fact that ILs solubilize high-M r carbohydrates to produce clear solutions, akin to those in obtained in LiCl/DMAc and TBAF/DMSO, has led to intensive research on biopolymer functionalization, in particular, acylation in these media.…”

Section: Synthesis Of Functionalized Carbohydrates In Ilsmentioning

confidence: 99%

“…

Section: Applications Of Ils In Carbohydrate Chemistry: a Window Of ...mentioning

confidence: 99%

“…Recycling of the IL was examined; the products were extracted with toluene, the IL was washed with water and passed through a pad of Celite, and the volatiles removed under reduced pressure. The benzylidenation reaction was repeated five times without loss in efficiency …”

Section: Applications Of Ils In Carbohydrate Chemistry: a Window Of ...mentioning

confidence: 99%

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Applications of Ionic Liquids in Carbohydrate Chemistry: A Window of Opportunities

et al. 2007

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Ionic liquids (ILs) are composed only of ions. Of special interest to this review are those where at least one ion (the cation) is organic and whose melting points are below or not far above room temperature. ILs are designated as "green" solvents because they have extremely low vapor pressure, are non-inflammable, and thermally and chemically stable. Therefore, many of them can be, in principle, recycled into the process indefinitely. The objective of the present review is to discuss different aspects of the use of ILs in carbohydrate chemistry, in particular, dissolution and functionalization of simple sugars, cyclodextrins, cellulose, starch, and chitin/chitosan. The molecular structure and synthesis of ILs most frequently employed in carbohydrate chemistry are discussed with an emphasis on imidazolium and pyridinium cations with different counterions. The physicochemical properties of ILs that are relevant to the dissolution and functionalization of carbohydrates, in particular their polarities and hydrogen-bonding abilities, are discussed. Dissolution of simple saccharides and biopolymers in ILs is presented with an emphasis on the mechanism of carbohydrate--IL interactions. Finally, the very interesting novel applications of the solutions obtained are addressed. These include, inter alia, spinning of the dissolved biopolymer into fibers, extrusion into slabs and rods, formation of matrixes for a myriad of substrates, including biomacromolecules, formation of nanocomposites, and functionalization to produce important derivatives. The use of ILs in many branches of science is expanding fast; it is hoped that this review will draw the attention of researchers to the "window of opportunities" that these green solvents open into carbohydrate chemistry.

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Section: Synthesis Of Functionalized Carbohydrates In Ilsmentioning

confidence: 99%

Section: Synthesis Of Functionalized Carbohydrates In Ilsmentioning

confidence: 99%

“…

Section: Applications Of Ils In Carbohydrate Chemistry: a Window Of ...mentioning

confidence: 99%

Section: Applications Of Ils In Carbohydrate Chemistry: a Window Of ...mentioning

confidence: 99%

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Applications of Ionic Liquids in Carbohydrate Chemistry: A Window of Opportunities

et al. 2007

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Three Solvent‐Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One‐Pot Generation of Orthogonally Protected Building Blocks

et al. 2015

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Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature. The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple experimental conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars

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