An efficient synthesis of short-chain sphingomyelin analogs and their susceptibility to hydrolysis catalyzed by sphingomyelinase

An efficient synthesis of (D)-erythro-sphingomyelin analogs was achieved via highly stereoselective reduction of 3-benzyl-4-(alkynyloxo)-oxazolidinone with diisobutylaluminum phenoxide reagent. The initial velocities of the hydrolysis of the (D)-erythro-derivatives catalyzed by B. cereus sphingomyelinase were more than 10 times faster than those of the (D)-threo-isomers.