PREPARATION OF THYMIDINE-4'-C-CARBOXYLIC ACID AND ITS DERIVATIVES

3',5'-Di-O-benzoyl-4'-C-hydroxymethylmidine (3) was prepared in four s teps from rt-butyldimethylsilyl)-4'-C-hydroxymethylthymidine (1). Oxid ation of 3 with pyridinium dichromate afforded 3',5'-di-O-benzoylthymi dine-4'-C-carboxylic acid (4) which on debenzoylation gave free thymid ine-4'-C-carboxylic acid, rahydropyrimidin-1-yl)tetrahydrofuran-2-carb oxylic acid, (5). Esterification of acid 5 with diazomethane afforded the methyl eater 6. Its isopropyl ester 7 was obtained by transesterif ication of the methyl ester 6. Reaction of ester 6 with ammonia and hy drazine led to the respective amide 8 and hydrazide 9. Upon reaction w ith 1,1'-carbonyldiimidazole, the protected acid 4 was converted into the corresponding imidazolide 11, which, without isolation, was treate d with glycinamide, dimethylamine and aminoethanol to give aminocarbon ylmethylamide 12a, N,N-dimethylamide 13a and hydroxyethylamide 14a, re spectivelg. The foe amides 12b, 13b and 14b were obtained by methanoly sis of corresponding benzoates with methanolic sodium methoxide. Neith er of the prepared compounds exhibited significant activity against HI V.