Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives.: Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration

The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.