Abstract
The synthesis of several C
60 derivatives containing a 6-(β-
d-glycopyranosylamino)pyrimidin-4-one unit and a C
60–uridine conjugate is described. The fullerene derivatives bearing a 4-(β-
d-glycopyranosylamino)pyrimidin-4-one moiety were synthesised by 1,3-dipolar cycloaddition reactions of C
60 with azomethine ylides generated in situ from the corresponding 5-formylpyrimidin-4-one derivatives and
N-methylglycine. The synthesis of the C
60–uridine conjugate involved the selective protection of the 2′- and 3′-hydroxyl groups of uridine, esterification, cyclopropanation of C
60 and, finally, the deprotection of the hydroxyl groups. One of the fullerene–glycopyranosylaminopyrimidin-4-one conjugates was characterised by single-crystal X-ray crystallography. Differentiation between pairs of diastereoisomers, for several fullerene derivatives, was achieved through the study of their gas-phase fragmentations.
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