Acyclic analogs of dideoxydidehydronucleosides
Tsytovich, A.V.; Kochetkova, M.V.; Philippov, D.V.; Mitsner, B.I.; Shvets, V.I.
Nucleic Acids Symposium Series 24: 23-24
1991
ISSN/ISBN: 0261-3166 PMID: 1841301 Document Number: 380544
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.