14048-58-9

Usage

InChI:InChI=1/C10H14O7/c1-4-5(10(15)16)2-7(17-4)9(14)8(13)6(12)3-11/h2,6,8-9,11-14H,3H2,1H3,(H,15,16)/p-1/t6-,8+,9-/m1/s1

Upstream product

• 81703-84-6 1-{2-methyl-5-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]-3-furyl}-1-ethanone 
• 17651-08-0 methyl 5-(D-arabino-tetroxybutyl)-2-methyl-3-furoate 
• 81661-22-5 5-(D-arabino-tetroxybutyl)-3-carbamoyl-2-methyl-furan 
• 50-99-7 D-glucose 
• 50-99-7 D-glucose 
• 110392-87-5 benzyl 2-methyl-5-(1,2,3,4-tetrahydroxybutyl)furan-3-carboxylate 
• 93253-62-4 2-methyl-5-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-3-furoic acid 
• 59-23-4 D-Galactose 
• 47001-46-7 ethyl 2-methyl-5-[(1S,2S,3R)-1,2,3,4-tetrahydroxybutyl]-3-furoate 
• 81661-23-6 5-(D-arabino-tetroxybutyl)-2-methyl-3-nitrile-furan 
• 3351-43-7 ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate 

Downstream Products

• 1125-59-3 5-Formyl-2-methyl-furan-3-carbonsaeure 

Relevant academic research and scientific papers

Solution and solid phase synthesis of hetarylene-carbopeptoids. A new type of peptidomimetics

Ready access to a new class of peptidomimetics has been demonstrated by the synthesis of hetarylene-carbopeptoids using hydroxyalkylfuran-aminoacids 7 as novel scaffold.

Synthesis, biological evaluation, wac and NMR studies of s-galactosides and non-carbohydrate ligands of cholera toxin based on polyhydroxyalkylfuroate moieties

The synthesis of several non-carbohydrate ligands of cholera toxin based on polyhydroxyalkylfuroate moieties is reported. Some of them have been linked to D-galactose through a stable and well-tolerated S-glycosidic bond. They represent a novel type of non-hydrolyzable bidentate ligand featuring galactose and polyhydroxyalkylfuroic esters as pharmacophoric residues, thus mimicking the GM1 ganglioside. The affinity of the new compounds towards cholera toxin was measured by weak affinity chromatography (WAC). The interaction of the best candidates with this toxin was also studied by saturation transfer difference NMR experiments, which allowed identification of the binding epitopes of the ligands interacting with the protein. Interestingly, the highest affinity was shown by non-carbohydrate mimics based on a polyhydroxyalkylfuroic ester structure. No carbs here: Saturation transfer difference (STD) NMR studies of bidentate ligands of cholera toxin (see figure, WAC = weak affinity chromatography) show the methylfuran moiety as the main contact point in the interaction with the toxin. Several polyhydroxyalkylfuroate-based structures are synthesized and analyzed and show similar or even better affinity than the bidentate ligands. They constitute the first examples of non-carbohydrate ligands for cholera toxin. Copyright

Hetaryleneaminopolyols and hetarylenecarbopeptoids: A new type of glyco- and peptidomimetics. Syntheses and studies on solution conformation and dynamics

Ready access to a new class of oligomers has been demonstrated by the synthesis of hetaryleneaminopolyols and hetarylenecarbopeptoids using 3-hydroxymethyl-5-(4-amino-4-deoxy-D-arabinotetritol1-yl)-2-methylfuran and 5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methyl-3-furoic acid as novel scaffolds. The conformational behavior of peptidomimetics 22, 23, 25, 26, and 36 have been analyzed by NMR spectroscopy and extensive molecular dynamics simulations. MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provide a population distribution of conformers which satisfactorily agrees with the experimental NMR data for the torsional degrees of freedom of the molecule.

PREPARATION OF FURAN DERIVATES FROM PENTOSES AND HEXOSES. STUDY OF THE ANHYDRIZATION OF THE TETRAHYDROXYLATED CHAIN AT α POSITION

The reaction of pentoses and hexoses with active methylene compounds in presence of an ethanolic solution of a Lewis acid or mixtures of aquenous acids leads to polyfunctional furanic derivatives in wich a polyhydroxylated chain exists in α position.When