Improved synthesis of cord factor analogues via the Mitsunobu reaction.
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.
D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D003311:Cord Factors / Q000138:chemical synthesis*; D006017:Glycolipids / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D003311:Cord Factors; D006017:Glycolipids; D007202:Indicators and Reagents