Photobromination of carbohydrate derivatives. Part 4. Observations on some glucopyranoside esters; a simple route to aryl α-L-ido-pyranosides

Abstract

Photobromination of methyl tetra-O-benzoyl-β-D-glucopyranoside gives 2,3,4,6-tetra-O-benzoyl-2-bromo-D-glucono-1,5-lactone as the main product following hydrogen abstraction at C-1, but similar treatment of aryl β-D-glucopyranoside esters causes abstraction at C-5 and leads to 5-bromo-derivatives. Reduction of these latter products offers a simple route to aryl α-L-idopyranosides which provide means of access to analytical substrates for L-iduronidase.