Novel synthesis of L-iduronic acid using trehalose as the disaccharidic starting material

Article abstract of DOI:10.1016/S0040-4039(98)02662-8

For the preparation of L-iduronic acid, trehalose was converted into a derivative of a novel disaccharide, β-L-idopyranosyl β-L-idopyranoside, through diastereoselective hydroboration of the 5,5'-di-eno intermediate. The 6- and 6'-hydroxy groups were then oxidized in two steps to give a disaccharide composed of 2 units of L-iduronate moieties, which underwent acidic cleavage of the glycosidic bond to give the target compound.