Isomannide and Isosorbide

Koert, Ulrich

doi:10.1002/047084289x.rn01380

Cited by 7 publications

(10 citation statements)

References 33 publications

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“…Isomannide and isosorbide ( Figure 3 ) are two renewable, inexpensive, and commercially available chiral compounds derived from the dehydration of d -mannitol and d -sorbitol, respectively, obtained as waste products during the processing of corn oil [ 64 ]. These building blocks are characterized by a cis -fused bicyclic rigid structure and by two hydroxyl groups at C3 and C6 .…”

Section: Synthesismentioning

confidence: 99%

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

2021

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Carbohydrates represent a promising option in transitioning from oil-based chemical resources to renewable ones, with the goal of developing chemistries for a sustainable future. Cellulose, hemicellulose, and largely available monosaccharides already provide useful chemical building blocks, so-called platform chemicals, such as levulinic acid and hydroxymethyl furfural, as well as solvents like cyrene or gamma-valerolactone. Therefore, there is great anticipation for novel applications involving materials and chemicals derived from sugars. In the field of ionic liquids (ILs), sugar-based ILs have been overlooked for a long time, mainly on account of their multistep demanding preparation. However, exploring new strategies for accessing sugar-based ILs, their study, and their exploitation, are attracting increasing interest. This is due to the growing concerns about the negative (eco)toxicity profile of most ILs in conjunction with their non-sustainable nature. In the present review, a literature survey concerning the development of sugar-based ILs since 2011 is presented. Their preparation strategies and thermal behavior analyses, sorted by sugar type, make up the first two sections with the intention to provide the reader with a useful guide. A final overview of the potential applications of sugar-based ILs and their future perspectives complement the present analysis.

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Section: Synthesismentioning

confidence: 99%

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

2021

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“…Starting from these considerations we reasoned that, in the search of new CPL‐emitting excimers, great advantages could be taken starting from isohexides as the central chiral scaffolds. Isohexides, namely isomannide (1) and isosorbide (2), also known as (3R,3aR,6R,6aR)‐hexahydrofuro[3,2‐b]furan‐3,6‐diol and (3R,3aR,6S,6aR)‐hexahydrofuro[3,2‐b]furan‐3,6‐diol (Figure 1), are important by‐products of the starch industry, arising from dehydration of D‐mannitol and D‐sorbitol [41] …”

Section: Introductionmentioning

confidence: 99%

“…Isohexides, namely isomannide (1) and isosorbide (2), also known as (3R,3aR,6R,6aR)-hexahydrofuro [3,2b]furan-3,6-diol and (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6diol (Figure 1), are important by-products of the starch industry, arising from dehydration of D-mannitol and D-sorbitol. [41] These commercially available starting materials provide an easy and inexpensive access to optically pure functionalized compounds. Indeed, through a simple derivatization of the two hydroxyl groups, the characteristic chiral cavity of their scaffold (Figure 1) can be functionalized, thus leading to new compounds, whose properties depend not only on the nature of the introduced moieties, but also on the different stereochemistry of the native hydroxyl groups.…”

Section: Introductionmentioning

confidence: 99%

Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources

Zullo

Iuliano

Zinna

2022

Chemistry A European J

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Organic compounds showing circularly polarized luminescence (CPL) are at the forefront of novel applications and technologies. Here we show the synthesis and chiroptical properties of pyrene and perylene derivatives of inexpensive chiral scaffolds: isomannide and isosorbide. Low‐intensity ECD spectra were obtained, suggesting the absence of chromophore interaction in the ground state, except in the case of isomannide bis‐perylenecarboxylate, whose ECD spectrum showed a positive exciton couplet. All isomannide derivatives, with the only exception of the one containing a pyrenecarboxylate and a perylenecarboxylate, exhibited excimer CPL spectra, whereas isosorbide derivatives did not show any CPL. Isomannide derivatives bearing two pyrenecarboxylate or two pyrenylacetate groups showed positive CPL emission with dissymmetry factors up to 10−2, which depends on the conformational freedom of the appended units. The CPL sign, Stokes shift and order of magnitude of dissymmetry factor were reproduced by excited‐state calculations on a representative compound. Interestingly, the mixed derivative containing pyrenic units with different spacing from the isomannide scaffold showed an oppositely signed excimer band with respect to the homo‐substituted derivatives.

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“…They are renewable, inexpensive, and commercially available chiral compounds derived from the dehydration of sorbitol and mannitol, respectively, which are waste products formed during the processing of corn oil and byproducts from the starch industry. 10 Isomannide (1) and isosorbide (2) possess a vaulted structure due to the cis junction of the two tetrahydrofuran rings with two hydroxyl groups that in isomannide are directed toward the inner of the chiral cavity (Figure 1). Thanks to these stereochemical features, isomannide derivatives constitute real chiral pockets, inside which enantioselective processes can take place with high effectiveness.…”

mentioning

confidence: 99%

An Efficient and Practical Chemoenzymatic Route to (3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-Aminoisomannide) from Renewable Sources

Zullo¹,

Petri²,

Iuliano³

2021

SynOpen

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The synthesis of 6-aminoisomannide is easily achieved starting from the renewable, inexpensive and commercially available isosorbide, in 66% overall yield. A biocatalysed highly regioselective acetylation of the 3-endo hydroxyl group of isosorbide was followed by the stereospecific interconversion of the 6-exo hydroxyl group into azido group, through reaction with trifluoromethanesulfonic anhydride followed by nucleophilic displacement of the triflate group by sodium azide. Finally, reduction of the azido group and deacetylation of the 3-hydroxy group were performed one pot by using LiAlH4.

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Isomannide and Isosorbide

Cited by 7 publications

References 33 publications

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources

An Efficient and Practical Chemoenzymatic Route to (3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-Aminoisomannide) from Renewable Sources

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