5′-Benzoyl-2′α-bromo-3′-O-methanesulfonylthymidine: A superior nucleoside for the synthesis of the anti-AIDS drug D4T (Stavudine)

The anti-AIDS drug d4T is prepared in 75% overall yield starting from the readily available ribonucleoside 5-methyluridine (1). The key step in this new synthesis is the zinc-induced reductive elimination of the bromomesylate 4, which affords d4T without nucleoside bond cleavage. A facile procedure for the deprotection/isolation of this highly water soluble product is also described.