SYNTHESIS OF CERTAIN 5-SUBSTITUTED 2'-DEOXYTUBERCIDIN DERIVATIVES

Abstract

The synthesis of the 7-deaza-2'-deoxy-adenine derivatives 7b-d with chloro, bromo, or methyl substituents at C(5) is described. Glycosylation of the 5-substituted 4-chloropyrrolo[2,3-d]pyrimidines 4b-d with 2-deoxy-3,5-di-O-(4-toluoyl)-alpha -D-erythro-pentofuranosyl chloride (3) gave the beta-D-nucleosides 5b-d, exclusively. They were deblocked (-->6b-d) and converted into the tubercidin derivatives 7b-d.