Synthesis of purine and primidine nucleosides analogues

Abstract EN

The theophlline and thymine nucleosides analogues (8) and (9) were obtained via reaction of diacetone glucose (1) with dimethyl sulphoxide and acetic anhydride to give diacetone glucose-3-ulose derivative (2).

Reaction of compound (2) with dimethylmalonate yielded the 3-C-dimethylmalonyl derivative (3).

The isopropylidene at 5, 6-position was removed with acetic acid followed by periodate oxidation and borohydride reduction to give the ribo derivative (5).

The 3, 5- dihydroxy groups were protected with benzoyl groups using benzoyl chloride to give the 3,5-dibenzoate derivatives (6).

Treatment of compound (6) with mixture of acetic acid, acetic anhydride and few drops of sulfuric acid to gave the 1, 2-di-Oacetylated compound (7).

When compound (7) was allowed to react with theophlline and silylated thymine, compounds (8) and (9) were obtained.

Deprotection of compounds (8) and (9) under basic condition yield the new nucleosides analogues (10) and (11).