title: Acyclic analogs of dideoxydidehydronucleosides.
abstract: A new type of acyclic nucleoside analogs is proposed, containing C5 hydroxyalkyl fragments, where the distance between 5'-hydroxyl group and the heterocyclic moiety corresponds to that in dideoxydidehydronucleosides (as confirmed by computer modelling). Condensation between 5-0-acetyl-1-bromo-2-pentene and persilylated heterocyclic bases (pyrimidines and guanine) or adenine sodium salt gives rise to the acyclic nucleosides (5a-d, 6a-d) with the yields ranging from 40% up to 85%. Deprotection by NH3/MeOH results in the desired nucleosides (1a-d, 2a-d) formation.
authors.affiliation: Department of Biotechnology, Lomonosov Institute of Fine Chemical Technology, Moscow, USSR.
authors.forename: A V
authors.initials: AV
authors.lastname: Tsytovich
authors.forename: M V
authors.initials: MV
authors.lastname: Kochetkova
authors.forename: D V
authors.initials: DV
authors.lastname: Philippov
authors.forename: B I
authors.initials: BI
authors.lastname: Mitsner
authors.forename: V I
authors.initials: VI
authors.lastname: Shvets
mesh_terms: D006147:Guanine; D007202:Indicators and Reagents; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines
chemical_list: D007202:Indicators and Reagents; D009705:Nucleosides; D011743:Pyrimidines; D006147:Guanine