Efficient syntheses of 1 -S-alkyl-1-thio- l-ribitols, d-lyxitols and l-xylitols from d-pentono-1,4-lactones

Abstract

The thioalkylation of unprotected 5-bromo-5-deoxy- d-ribono, d-arabinono, and d-xylono-1,4-lactone was performed with the alkylthiol-sodium hydride reagent. The corresponding 5- S-alkyl-5-thio- d-pentono-1,4-lactones were isolated in good yields (82–95%). Reduction with NaBH 4 of these derivatives gave the 1- S-alkyl-1-thio- l-ribitols, d-lyxitols and l-xylitols in 85–96% yields.