| Abstract: | Treatment of trehalose with triphenylphosphine, diisopropyl azodicarboxylate and beta-O-tetrahydropyran-2-ylmycolic acid in 1:1 hexamethylphosphoric triamide/dichloromethane, followed by removal of the tetrahydropyranyl protecting group, gave cord factor (1) in good yield, under exceptionally mild conditions. Two new cord factor analogues were similarly prepared from beta-O-methylmycolic acid and from the alpha, beta-unsaturated 'anhydro' mycolic acid respectively. The procedure, employing excess trehalose, can also be used for the synthesis of trehalose monomycolates in good yield. No protection of the carbohydrate is required. |
