H. Hrebabecky et A. Holy, PREPARATION OF THYMIDINE-4'-C-CARBOXYLIC ACID AND ITS DERIVATIVES, Collection of Czechoslovak Chemical Communications, 62(7), 1997, pp. 1128-1135
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.