Acyclic analogs of dideoxydidehydronucleosides.
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.
Tsytovich
A V
AV
Department of Biotechnology, Lomonosov Institute of Fine Chemical Technology, Moscow, USSR.
Kochetkova
M V
MV
Philippov
D V
DV
Mitsner
B I
BI
Shvets
V I
VI
D006147:Guanine; D007202:Indicators and Reagents; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines
D007202:Indicators and Reagents; D009705:Nucleosides; D011743:Pyrimidines; D006147:Guanine