186539-89-9

Upstream product

• 75-03-6 ethyl iodide 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 65877-24-9 methyl 3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 186539-87-7 methyl 2-O-ethyl-3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside 

Downstream Products

• 1333398-05-2 methyl 4,6-O-(R)-benzylidene-2-O-ethyl-α-D-arabinohexopyranosid-3-ulose 

Relevant academic research and scientific papers

New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

New d-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene).

Analysis of the binding specificities of oligomannoside-binding proteins using methylated monosaccharides

The binding specificities of the closely related lectins from Canavalia ensiformis and Dioclea grandiflora were examined using specifically O-alkylated mono- and disaccharides. Both lectins accept any substitution at the monosaccharide C2 hydroxyl group. The binding energy of C2-alkylated ligands-concanavalin A complexes increases by 1 kcal mol-1 for the C2-O-ethyl ligand, while the binding energies of the corresponding complexes with the Dioclea lectin are identical. Both lectins accept methyl, but not ethyl, substitution of the C3 hydroxyl, in contrast to earlier reports. The results are interpreted in terms of existing models of the concanavalin A binding site. While the results are consistent with a model of the concanavalin A extended binding site that places the non-reducing terminus of all disaccharides in the monosaccharide binding site, they point to the dangers of interpreting the binding behavior of unnatural saccharide ligands on the basis of crystallographic data obtained with native ligands.