AN EFFICIENT SYNTHESIS OF Î'ETA-L-5-[(E)-2-BROMOVINIL)-1-((2S,4S)-2-(HYDROXYMETHYL)-1,3-(DIOXOLANA-4-YL) URACYL)] (L-BHDU) VIA PURE CHIRAL L-DIOXOLANA

Abstract

The present invention relates to a novel method for synthesizing L-BDHU and related starting materials and intermediate compounds from (7?J-2,2-dimethyl-1,3-dioxolane-4-carboxylate (7) in only 7 steps. The invention eliminates the expensive chiral purification of L-dioxolane (11), resulting in an enantiomerically enriched compound (ee > 99%). The optically pure compound 11 is utilized to construct L-BHDU (15) and its monophosphate drug precursor (POM-L-BHDU, 22). New synthetic methods and new intermediate compounds represent additional embodiments of the present invention.