Facile Preparation of Peracetates and Per-3-bromobenzoates of α-Mono- and Disaccharides

Abstract

A simple and convenient method for the preparation of fully acetylated and (3-bromo)benzoylated α-monosaccharides and disaccharides through vigorous mechanical mixing of solid reactants on a high speed shaker is described. Using this technique a variety of α‑acylated sugars are prepared, including penta-O-acetyl-α-D-galactopyranose, penta-O-acetyl-α-D-glucopyranose, penta-O-acetyl-α-D-mannopyranose, octa-O-acetyl-α-lactose, penta-O-(3-bromo)benzoyl-α-D-galactopyranose, penta-O-(3-bromo)benzoyl-α-D-gluco-pyranose, penta-O-(3-bromo)benzoyl-α-D-mannopyranose, and octa-O-(3-bromo)benzoyl-α-lactose.

On the investigation of hybrid quinones: synthesis, electrochemical studies and evaluation of trypanocidal activity

“…These alkynecarbohydrate derivatives were obtained using two different methods of acetylation. 48,49 For the glucose and galactose derivatives, D-glucose and D-galactose were subjected to peracetylation with NaOAc in acetic anhydride, and the compounds were prepared in moderate yields. For the mannose derivative, catalytic amounts of I 2 were used instead of NaOAc.…”

A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

“…For comparison, per(3-bromo)benzoates of α-D-lactose, α-D-glucose, α-D-galactose, α-D-mannose and β-D-mannose [ 21 ] were heated with AlCl 3 at 110 °C. It was found that all of the anomeric acyl groups ( i.e.…”

“…In addition, the anomeric configuration for β-D-glucose and β-D-galactose derivatives have been inverted in the respective products, e.g., from β-D-glucose pentaacetate to 2,3,4,6-tetra- O -acetyl-α-D-glucopyranose. While α-D-glucose and α-D-galactose per(3-bromo)benzoates [ 21 ] also undergo a similar debenzoylation at the anomeric position, the original α-configuration is retained in the corresponding products. However, the debenzoylation of α-D-mannose per(3-bromo)benzoate affords 2,3,4,6-tetra- O -(3-bromo)benzoyl-β-D-mannopyranose, indicating the conversion of configuration at the anomeric position during the debenzoylation.…”

The Use of Exoglycosidases for the Assay of Two New Enzymatic Substrates, b-D-xylopyranosyl-4-nitrocatechol-1-yl and a-lactosyl-4-nitrocatechol-1-yl

“…This can be explained only admitting a limited glycolytic activity of promotor. 1 H NMR spectra of lactoside indicated it to be the alpha anomer 3 [18].…”