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

For the preparation of L-iduronic acid, trehalose was converted into a deri vative of a novel disaccharide, beta-L-idopyranosyl beta-L-idopyranoside, t hrough diastereoselective hydroboration of the 5, 5'-di-eno intermediate. T he 6- and 6'-hydroxy groups were then oxidized in two steps to give a disac charide composed of 2 units of L-iduronate moieties, which underwent acidic cleavage of the glycosidic bond to give the target compound. (C) 1999 Else vier Science Ltd. All rights reserved.