Synthesis of 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl(thymine (d4T; stavudine) from 5-methyluridine
A practical synthetic method of d4T (3) from 5-methyluridine (2a) was developed. The Marumoto-Mansuri method was modified using 2',3'-O-methoxyethylidene-5-methyluridine (10) as an intermediate to afford 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine (6a) in high yield with less formation of byproducts. The reaction mechanism was also discussed.