124674-81-3Relevant academic research and scientific papers
A novel method for the direct activation of aldehydes. Synthesis of carbohydrate acetals
Hodosi, Gyoergy
, p. 6129 - 6132 (1994)
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.
Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers
Belmessieri, Dorine,Gozlan, Charlotte,Duclos, Marie-Christine,Molinier, Valérie,Aubry, Jean-Marie,Dumitrescu, Oana,Lina, Gérard,Redl, Andreas,Duguet, Nicolas,Lemaire, Marc
, p. 98 - 106 (2017)
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.
ANTIBACTERIAL COMPOSITION CONTAINING AN ISOMER MIXTURE OF MONOSACCHARIDE ALKYL MONOACETALS OR MONOETHERS
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Paragraph 0125-0126, (2018/01/11)
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.
Catalytic reductive cleavage of methyl α-d-glucoside acetals to ethers using hydrogen as a clean reductant
Gozlan, Charlotte,Lafon, Romain,Duguet, Nicolas,Redl, Andreas,Lemaire, Marc
, p. 50653 - 50661 (2015/02/19)
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
TMDS as a dual-purpose reductant in the regioselective ring cleavage of hexopyranosyl acetals to ethers
Zhang, Yin-Jie,Dayoub, Wissam,Chen, Guo-Rong,Lemaire, Marc
experimental part, p. 1960 - 1966 (2012/05/20)
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
Mesogenic 4-O-Alkyl-D-Glucose via Methyl 4,6-O-Alkylidene-D-glucopyranosides
Dahlhoff, Wilhelm V.,Riehl, Klaus,Zugenmaier, Peter
, p. 1063 - 1068 (2007/10/02)
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
