Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents

Ranoux, Adeline; Lemiègre, Loı̈c; Benvegnu, Thierry

doi:10.1007/s11426-010-4055-3

Cited by 10 publications

(6 citation statements)

References 16 publications

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“…C 4 Glu does not solubilize efficiently CA and only few amounts of UA. The used C 4 Glu concentration (30 wt %) is indeed below the MHC according to the literature (2.0 mol/L, 43 wt %), contrary to i C 5 Xyl, C 7 Glu, C 6,–2 Glu, and C 8/10 Gly (Table ). C 7 Glu solubilizes the highest amount of both CA (30.4 g/L) and UA (20.1 g/L), while i C 5 Xyl solubilizes the lowest amounts of CA (14.1 g/L) and UA (∼0.4 g/L).…”

Section: Results and Discussionmentioning

confidence: 77%

Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

Mazaud

Lebeuf

Pierlot

et al. 2021

ACS Sustainable Chem. Eng.

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Rosemary (Rosmarinus officinalis L.) is a Mediterranean herb known for its high antioxidant power that has been widely attributed to carnosic acid (CA). Passive extractions of CA have been performed in water by using five commercially available short-chain alkyl polyglycosides (APG) with alkyl chain lengths ranging from 4 to 10 carbon atoms and polar heads composed of pentoses and/or glucoses. APGs are nontoxic amphiphiles with high biodegradability. Their solubilizing capacity for CA has been determined, highlighting heptyl glucoside (C7Glu) as the most efficient one, followed by 2-ethylhexyl glucoside (C6,–2Glu) and isoamyl xyloside (iC5Xyl). However, iC5Xyl exhibited the highest selectivity toward CA solubilization as compared to ursolic acid (UA), a potential coextracted compound of rosemary leaves. In addition, it was found to be the most efficient amphiphile to extract CA from both ground and whole rosemary leaves. To optimize the maceration process and the recovery of the extract, a full factorial design 24 was performed investigating iC5Xyl concentration, temperature, stirring, and extraction time. A high concentration of hydrotrope was found to be the most important condition to optimize the maceration step, while the temperature particularly increases the yield, but in detriment of the CA content in the final dried extract.

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Section: Results and Discussionmentioning

confidence: 77%

Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

Mazaud

Lebeuf

Pierlot

et al. 2021

ACS Sustainable Chem. Eng.

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“…484−489 Horner−Wadsworth−Emmons reaction of lactose 572 with β-ketophosphonate 573 under basic conditions provided β-C-glucoside 574 (67%). 490,491 Aldol reaction of D-deoxyribose 575 with acetoacetic ester 576 catalyzed by i Pr 2 NEt and 2-pyridone led to hemiketal 577 with high diastereoselectivity (45%, dr > 49:1). 492 Under the promotion of L-proline and DBU, the Knoevenagel−Michael cascade reaction of D-ribose 578 with dimethyl 3-oxoglutarate 579 gave C-glycoside 580 (86%, dr > 49:1), whereas the aldol-Michael reaction of 578 with acetone 581 provided a mixture of αand β-C-glycosides 582 and 583 and the hemiketal 584 in a 69% overall yield.…”

Section: C-glycosylation With Sugar Lactolsmentioning

confidence: 99%

“…Direct use of unprotected sugar lactols for coupling with C -nucleophiles represents an attractive approach en route to C -glycosides. − Henry condensation of glucose 566 with nitromethane under the catalysis of sodium methoxide followed by reflux in water to promote dehydration and cyclization afforded β- C -glucoside 567 in 53% yield (Scheme ). − Coupling of glucose 566 with pentane-2,4-dione 568 in the presence of sodium bicarbonate proceeded through Knoevenagel reaction and intramolecular Michael cyclization to give β- C -glucoside 569 in excellent yield. ,, Reactions of other types of unprotected sugar lactols such as 2-acetamido sugars, heptoses, xylose, and galactose with C -nucleophiles such as 1,3-dicarbonyl compounds and 1,3-oxazine-2-thiones in the presence of base (NaHCO 3 , Na 2 CO 3 , NaH, or KOH) or Lewis acid (InCl 3 , CoCl 2 ) also afforded the corresponding C -pyrano- or C -furanoglycosides in good yields with high β-stereoselectivities. ,− As an example of Sc(OTf) 3 -promoted C -glycosylation of unprotected sugar lactols with aryl compounds, direct glycosylation of glucose 566 with 570 gave β- C -aryl glycoside 571 (65%). − Horner–Wadsworth–Emmons reaction of lactose 572 with β-ketophosphonate 573 under basic conditions provided β- C -glucoside 574 (67%). , Aldol reaction of d -deoxyribose 575 with acetoacetic ester 576 catalyzed by i Pr 2 NEt and 2-pyridone led to hemiketal 577 with high diastereoselectivity (45%, dr > 49:1) . Under the promotion of l -proline and DBU, the Knoevenagel–Michael cascade reaction of d -ribose 578 with dimethyl 3-oxoglutarate 579 gave C -glycoside 580 (86%, dr > 49:1), whereas the aldol-Michael reaction of 578 with acetone 581 provided a mixture of α- and β- C -glycosides 582 and 583 and the hemiketal 584 in a 69% overall yield. − Other amine-mediated aldol-Michael reactions of unprotected ketoses or 2- N -acyl-aldohexoses with acetone 581 have also been reported for the synthesis of C -glycosides. , Recently, Cu(I)-catalyzed dehydrative C -glycosylation of unprotected 2-deoxy sugar 585 with acetophenone 586 in the presence of diphosphine ligand L1 was reported to give C -glycosi...…”

Section: C-glycosylation With Sugar Lactolsmentioning

confidence: 99%

Recent Advances in the Chemical Synthesis of C-Glycosides

2017

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Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C-C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg-Bäcklund rearrangement, and 1,2-Wittig rearrangement, which usually involve concerted pathways, constitute another category of C-glycosylations. An alternative to the C-glycosylations is the formation of pyranoside/furanoside rings after construction of the predetermined glycosidic C-C bonds, which might involve cyclization of acyclic precursors or D-A cycloadditions. Throughout, the stereoselectivity in the formation of the resultant C-glycosidic linkages is highlighted.

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“…Four products can be obtained ( or  of the C-pyranosides and Cfuranosides), with in most cases a strong or total selectivity in the -C-pyranosides. The reaction can be extended to disaccharides and a wide range of chain lengths, and has also been conducted under solvent free conditions[32,261,262].…”

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confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

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GLOSSARY Carbohydrates are a family of biomolecules, ubiquitous in Nature, based on a common polyhydoxylated backbone though varying in size (from small molecules to macromolecules), in fine structure (configuration and functionalization), and possessing a wide range of biological properties and roles making them indispensable to life. Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups. Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension. Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, terpenes. DEFINITION OF THE SUBJECT Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life, and must therefore be improved constantly in terms of environmental impact, sustainability and performance. One way towards more sustainable surfactants is the use of renewable resources as raw materials for their manufacture, in place of fossil ones. Since the structure of surfactant combines a polar part to a hydrophobic one, carbohydrates, which are very polar molecules, appear as ideal candidates for serving as renewable building blocks in the synthesis of bio-based surfactants. Developed first with the aim of providing added-value to some agricultural crops and by products, this strategy shows nowadays a rebirth in the context of green and sustainable chemistry. The chapter illustrates, from the chemical point of view, the diversity of molecular structures which belong to the family of carbohydrate-based surfactants.

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Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents

Cited by 10 publications

References 16 publications

Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

Recent Advances in the Chemical Synthesis of C-Glycosides

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

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