A Facile and Eco-Friendly Method for the Synthesis of 1,2-Orthoesters of Carbohydrates in Ionic Liquid

Radhakrishnan, K. V.; Sajisha, V. S.; Chacko, Jessy Maria

doi:10.1055/s-2005-864818

Cited by 15 publications

(5 citation statements)

References 7 publications

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“…The yield of the 1,2-orthoesters obtained varies from 52% (2-propanol) to 80% (4-penten-1-ol). Satisfactory yields were obtained for the reactions of galactose and mannose, 68−82% and 59−70%, respectively 10 Scheme for the synthesis of cyclic 1,2-orthoesters.…”

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

confidence: 99%

“…Satisfactory yields were obtained for the reactions of galactose and mannose, 68-82% and 59-70%, respectively. 156 Although strategies for the synthesis of oligosaccharides are well established, many are laborious and require purification of the reaction product after each step. 157,158 Recent advances include solid-phase synthesis, 159 the use of polymer-supported synthesis (polyethylene glycol, fluorinated supports), 160,161 and IL-supported synthesis.…”

Section: Synthesis Of Functionalized Carbohydrates In Ilsmentioning

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

confidence: 99%

Section: Synthesis Of Functionalized Carbohydrates In Ilsmentioning

confidence: 99%

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

et al. 2007

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“…These have included chiral epoxidations [102], reduction of aldehydes using trialkylborons [103], 1,3-dipolar cycloadditions [104], Baylis-Hillman reactions [28,105], Knoevenagel condensations [106], α-tosylation of enolizable ketones [107], Rosenmund-von Braun reactions [108], acetylation [109] and benzoylation [110] of nucleosides, aza-Markovnikov addition to alkenes [111], three component syntheses to give 3-alkyl-5arylmethylidene-1,3-thiazolidine-2,4-diones [112], conjugate addition of thiols to electron deficient alkenes [113], aromatic aminations [114], conversion of the acetates of Baylis-Hillman adducts to give trisubstituted alkenes [115], selective benzoylation of nucleosides with benzoyl cyanide [116], the synthesis of aromatic nitriles from aromatic aldehydes [117], the synthesis of N-substituted phthalimides [118], alkylation of thiazolidinediones [119], stereoselective conjugate additions [120], synthesis of 1,2-orthoesters of carbohydrates [121], Morita-Baylis-Hillman reactions [122], Huisgen cycloaddition to form 1,2,3-triazoles [123] and esterification of tertiary alcohols [124]. However, in each of these cases, no explanation for the different outcomes in ionic liquids was discussed.…”

Section: Other Organic Processes Affected By Ionic Liquidsmentioning

confidence: 99%

Understanding Organic Processes in Ionic Liquids: Achievements So Far and Challenges Remaining

Harper¹,

Kobrak

2006

MROC

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The use of ionic liquids as alternatives to traditional molecular solvents is a rapidly expanding field. Their many advantages, including negligible vapor pressures, tunable miscibilities and the ease of product isolation, mean that they have been considered (and shown to be effective) as solvents for a range of reactions. However, the outcomes of many of these organic processes differ on changing solvent to an ionic liquid. For these ionic liquid media to be truly considered as alternative solvents, these differences must be understood. This article seeks to extend this understanding by reviewing the variations in the outcome of organic processes along with the fundamental physical properties of ionic liquids that differ from molecular liquids. A case study on nucleophilic substitutions is used to demonstrate the usefulness of our approach.

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“…38 A facile synthesis of 1,2-orthoesters of carbohydrates in [bmim]PF 6 has been described by Radhakrishnan et al as a simpler and ecofriendly method. 39 The use of 1-butyl-3-methylimidazolium tetrafluoroborate as the reaction medium and iron(III) chloride hexahydrate as a catalyst has been employed for the efficient preparation of a,a 0 -bis(substituted benzylidene) cycloalkanones. 40 The intrinsic properties of the ionic liquids described above facilitate reaction work-up and recycling of the solvent.…”

mentioning

confidence: 99%

Synthesis of benzylidenated hexopyranosides in ionic liquids

Zhang¹,

Ragauskas²

2005

Carbohydrate Research

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A Facile and Eco-Friendly Method for the Synthesis of 1,2-Orthoesters of Carbohydrates in Ionic Liquid

Cited by 15 publications

References 7 publications

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

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

Understanding Organic Processes in Ionic Liquids: Achievements So Far and Challenges Remaining

Synthesis of benzylidenated hexopyranosides in ionic liquids

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