Efficent Synthesis of 5-(4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl))benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives

Abstract

Objective Synthesis of gastrodin intermediate 4-formylphenyl(2,3,4,6-O-tetraacetyl)-β-D-glucoside analogues. Methods 5-(4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)) benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives were synthesized by the Knoevenagel reaction of self-made 4-formylphenyl(2,3,4,6-O-tetraacetyl)-β-D-glucoside and 2,2-dimethyl-1,3-dioxane -4,6-dione in the presence of N-methylimidazole trifluoromethyl sulfonate. Results and conclusions five products of gastrodin intermediate analogues characterized by NMR and MS(ESI). The reaction has the advantages of high yields(76%～84%), mild conditions, simple operation and environmental friendliness. N-methylimidazole trifluoromethyl sulfonate could be recycled and reused several times without significant loss of its efficiency.