HClO4?SiO2 catalysed synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester: Application in the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside

Article abstract of DOI:10.1039/b810654a

A variety of alcohols react with 2,3,4,6-tetra-O-acetyl-1,5-anhydro-d- arabino-hex-1-enopyranose 1 in the presence of a catalytic amount of HClO ₄ supported on silica gel to give the corresponding alkyl 3-deoxy-hex-2-enopyranosides 2 in high yield, with short reaction times (10-45 mins) and good α-selectivity. Work-up merely involves filtration of the reagent, followed by chromatographic purification of the crude product. This methodology has also been employed in the synthesis of a bicyclic ether, a useful precursor for cyclic polyethers, and a 4-amino-C-glucoside. The 2008 Royal Society of Chemistry.