Synthesis of certain 5-substituted 2'-deoxytubercidin derivatives

Article abstract of DOI:10.1002/hlca.19940770403

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)-α-D-erythro-pentofuranosyl chloride (3) gave the β-D-nucleosides 5b-d, exclusively. They were deblocked (→ 6b-d) and converted into the tubercidin derivatives 7b-d.