GLYCOSYLATION OF 2-THIOURACIL DERIVATIVES. A SYNTHETIC APPROACH TO 3-GLYCOSYL-2,4-DIOXYPYRIMIDINES

Abstract Reaction of 6-aryl-5-cyano-2-thiouracils 2a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. However, their deacetylation with ammonia in methanol caused a cleavage of the S-glycosyl residue and gave the N-3 glycosylated analogues 6a-h.