- A novel method for the direct activation of aldehydes. Synthesis of carbohydrate acetals
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A new method for the activation of alkyl and aryl aldehydes to substituted succinimidomethanium salts for the synthesis of cyclic dioxane type acetals of carbohydrates is described.
- Hodosi, Gyoergy
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- Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers
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A series of amphiphilic methyl glucopyranoside ethers incorporating various alkyl chain lengths has been synthesized from commercially available methyl glucopyranosides following an acetalisation/hydrogenolysis sequence. The amphiphilic properties of ethers and acetal intermediates were evaluated. Both families exhibit excellent surfactant properties with a maximum efficiency obtained for compounds bearing a linear dodecyl chain (CMC = 0.012 mM, γsat.= 30 mN m?1). Antimicrobial activity studies revealed an efficient activity (0.03 MIC 0.12 mM) against Gram-positive bacteria such as Listeria monocytogenes, Enterococcus faecalis, Enterococcus faecium and Staphylococcus aureus. More importantly, these compounds were found to be active against multi-resistant strains such as vancomycin-, methicillin- and daptomycin-resistant strains. Finally, it was found that antimicrobial activities are closely related to physicochemical properties and are also influenced by the nature of the carbohydrate moiety.
- Belmessieri, Dorine,Gozlan, Charlotte,Duclos, Marie-Christine,Molinier, Valérie,Aubry, Jean-Marie,Dumitrescu, Oana,Lina, Gérard,Redl, Andreas,Duguet, Nicolas,Lemaire, Marc
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- ANTIBACTERIAL COMPOSITION CONTAINING AN ISOMER MIXTURE OF MONOSACCHARIDE ALKYL MONOACETALS OR MONOETHERS
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A bactericidal or bacteriostatic composition comprising an isomer mixture of monosaccharide alkyl monoethers or monoacetals, its use in the treatment or prevention of Gram-positive bacterial infections, its use as a hygiene or dermatological product for external use and a method for disinfecting surfaces.
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Paragraph 0125-0126
(2018/01/11)
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- Catalytic reductive cleavage of methyl α-d-glucoside acetals to ethers using hydrogen as a clean reductant
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The palladium-catalysed reductive cleavage of methyl glucoside acetals has been studied using hydrogen as a clean reducing agent. The reaction proceeds at 120 °C in cyclopentyl methyl ether (CPME) without acid co-catalyst. Under these conditions, the corresponding methyl glucoside monoethers were obtained with poor to good isolated yields (37-81%) and high selectivities (86-99%). This journal is
- Gozlan, Charlotte,Lafon, Romain,Duguet, Nicolas,Redl, Andreas,Lemaire, Marc
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p. 50653 - 50661
(2015/02/19)
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- TMDS as a dual-purpose reductant in the regioselective ring cleavage of hexopyranosyl acetals to ethers
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1,1,3,3-Tetramethyldisiloxane (TMDS) has been developed as an excellent dual-purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4,6-O-acetals with Cu(OTf)2 or AlCl3 to afford the corresponding prim
- Zhang, Yin-Jie,Dayoub, Wissam,Chen, Guo-Rong,Lemaire, Marc
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experimental part
p. 1960 - 1966
(2012/05/20)
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- Mesogenic 4-O-Alkyl-D-Glucose via Methyl 4,6-O-Alkylidene-D-glucopyranosides
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The 4,6-O-alkylidene derivatives (hexylidene-decylidene, 2a-e) are prepared by condensation of methyl α- or β-D-glucopyranoside 1 with alkanals in the presence of pyridinium tosylate.O-diethylborylation of 2 gives 3 which are allowed to react firstly with bromodiethylborane and subsequently with sodium triethylhydroborate to yield methyl 4-O-alkyl-D-glucopyranosides 5 after deborylation.Acid hydrolysis of 5 gives mesogenic 4-O-alkyl-D-gluocpyranoses 6a-e.The amphiphilic 6 exhibit the smectic A liquid crystalline phase on melting. - Key Words: Carbohydrates / 4-O-Alkyl-D-glucoses / Liquid crystals, smectic / Bromodiethylborane-sodium triethylhydroborate reducing system / Amphiphilic glucoses / X-ray diffraction, small angle
- Dahlhoff, Wilhelm V.,Riehl, Klaus,Zugenmaier, Peter
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p. 1063 - 1068
(2007/10/02)
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