One-step synthesis of β-C-glycolipid derivatives from unprotected sugars

Hersant, Yaël; Abou-Jneid, Robert; Canac, Yves; Lubineau, André; Philippe, Michel; Semeria, D.; Radisson, X.; Scherrmann, Marie‐Christine

doi:10.1016/j.carres.2003.11.007

Cited by 39 publications

(25 citation statements)

References 7 publications

(2 reference statements)

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“…[4][5][6][7] The synthesis relies on a Knoevenagel condensation between the carbanion of a β-diketone and the formyl group of an unprotected sugar. A C-xyloside alcohol resulting from the reduction of a β-keto-C-glycoside obtained by this method was found to stimulate sulfated glycosaminoglycan (GAG) synthesis: this has recently been developed in cosmetic skincare products as proXylane TM .…”

Section: Introductionmentioning

confidence: 99%

Horner–Wadsworth–Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One‐Step Access to C‐Glycoside Amphiphiles

Ranoux¹,

Lemiègre²,

Benoit³

et al. 2010

Eur J Org Chem

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Section: Introductionmentioning

confidence: 99%

Horner–Wadsworth–Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One‐Step Access to C‐Glycoside Amphiphiles

Ranoux¹,

Lemiègre²,

Benoit³

et al. 2010

Eur J Org Chem

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“…This is an advantageous ‘green chemistry’ method for the formation of anomeric carbon–carbon bonds under aqueous conditions, and is applicable with a wide range of non‐protected sugars 4, 5. The reaction is applicable to hexoses and pentoses,1–3 heptoses,6 N ‐acetamido sugars,7 and with both alkyl and cyclic diketones 1–3, 8, 9. For non‐cyclic diketones a mechanism has been proposed for this reaction; nucleophic attack on the carbohydrate anomeric carbon atom, followed by asymmetric loss of a carboxylated group 2, 3, 8.…”

Section: Methodsmentioning

confidence: 99%

Electron impact ion fragmentation pathways of peracetylated C‐glycoside ketones derived from cyclic 1,3‐diketones

Adeuya

Price

2009

Rapid Comm Mass Spectrometry

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Monosaccharide C-glycoside ketones have been synthesized by aqueous-based Knoevenagel condensation of isotopically labeled and unlabeled aldoses with cyclic diketones, 5,5-dimethyl-1,3-cyclohexanedione (dimedone) and 1,3-cyclohexanedione (1,3-CHD). The reaction products and their corresponding acetylated analogs produce characteristic molecular adduct ions by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-TOF MS). Analysis of the peracetylated C-glycosides by electron ionization (EI) gas chromatography/mass spectrometry (GC/MS) revealed diagnostic fragment ions that have been used to deduce the EI fragmentation pathways and the structure of each C-glycoside ketone. Characteristic gluco- and ribo-specific ions were observed at m/z 350 and 278, respectively. Ions common to both carbohydrate fragmentation pathways were observed at m/z 193 and 169 for the dimedone-C-glycosides, and m/z 165 and 141 for the 1,3-CHD-C-glycosides. Ions with m/z 169 and 141 retain the anomeric carbon (carbon-1) of the original sugar, while m/z 193 and 165 are shown to retain carbons-1, 2, and 3.

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“…However, only a few methodologies [3][4][5][6] are applicable in aqueous media or from native sugars. Our research group started a program concerning the synthesis of C-glycoside amphiphiles to determine their potential applications as interfacial agents.…”

Section: Introductionmentioning

confidence: 99%

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

2010

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International audienceThis work presents expeditious synthesis of C-glycoside amphiphiles in aqueous media from unprotected di- or mono-saccharides. A Horner-Wadsworth-Emmons/Michael addition/Barbier allylation sequence led to C-glycosides that exhibit hydrotropic properties. The hydrotropic and solubilizing properties of these homoallylic alcohols including a β-C-glycoside moiety as well as additional β-C-glycosidic ketones with a short (C7) alkyl chain are also described and compared with those of commercial O-glucoside references

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One-step synthesis of β-C-glycolipid derivatives from unprotected sugars

Cited by 39 publications

References 7 publications

Horner–Wadsworth–Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One‐Step Access to C‐Glycoside Amphiphiles

Horner–Wadsworth–Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One‐Step Access to C‐Glycoside Amphiphiles

Electron impact ion fragmentation pathways of peracetylated C‐glycoside ketones derived from cyclic 1,3‐diketones

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

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