Synthesis of a deoxynojirimycin analogue from castanospermine

Abstract

Ring cleavage of 1,6- O, O- bis- t-butyldimethylsilylcastanospermine 3 with methyl chloroformate followed by deprotection with tetrabutylammonium fluoride gave (1S,6S,7R,8R,8aR)-1-(2′-chloroethyl)-1,5,6,7,8,8a-hexahydro-6,7,8-trihydroxy-3 H-furo[3,4- a]pyridin-3-one 5. Refluxing 5 with potassium t-butoxide, followed by the addition of NaOH and futher refluxing yielded the deoxynojirimycin analogue (1′S,2R,3R,4R,5S)-2-(1′-hydroxy-2′-propenyl)-piperidine-3,4,5-triol 2.