(E)-5-(2-Bromovinyl)-2'-deoxy-4'-thiouridine (S-BVDU) is a potent antiherpesvirus agent and its use in gene therapy as an anticancer agent has recently been described. We here outline 2 efficient methods for the synthesis of S-BVDU. The decision as to which method is to be used depends upon the starting materials available but starting from BVU, an overall yield of beta-nucleoside of 35% can be expected. From 5-ethyl-2'-deoxy-4'-thiouridine, radical bromination using bromine will give a quantitative conversion to S-BVDU if unreacted starting material is recycled (50%) or using N-bromosuccinimide, a one step yield in excess of 80% can be obtained.

No abstract

Efficient Syntheses of (E)-5-(2-Bromovinyl)-2'-deoxy-4'-thiouridine; a Nucleoside Analogue with Potent Biological Activity.-Two efficient, alternative routes to the synthesis of the title thiouridine [cf. protected precursors (VII) and (X)], one of the most potent and selective antiherpesvirus compounds known, are developed. -(BASNAK, I.; OTTER, G. P.; DUN-COMBE, R. J.; WESTWOOD, N. B.; PIETRARELLI, M.; HARDY, G. W.; MILLS, G.; RAHIM, S. G.; WALKER, R. T.; Nucleosides Nucleotides 17 (1998) 1-3, 29-38; Sch. Chem., Univ. Birmingham, Edgbaston, Birmingham B15 2TT, UK; EN)