The regiospecific one-pot phosphorylation of either the 5'- or 2'-hydroxyl in 3'-deoxycytidines without protection: critical role of the base.
We report methodology which enables direct phosphorylation of 3'-deoxycytidine exclusively either at the 5'-hydroxyl or the 2'-hydroxyl. Protection of the base is not required. Standard phosphoramidochloridates in combination with pyridine and tert-butyl magnesium chloride is employed, in which the ratio of nucleoside to Grignard reagent is crucial. These findings, which appear to be general for 3'-deoxycytidines, are not applicable to 3'-deoxyuridine or 3'-deoxyguanosine.
Howes
Peter D
PD
Department of Metabolic and Viral Chemistry, MV CEDD, GlaxoSmithKline, Stevenage, UK. pdh4343@gsk.com
Slater
Martin J
MJ
Wareing
Katrina
K
D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006900:Hydroxylation; D007202:Indicators and Reagents; D010766:Phosphorylation; D013237:Stereoisomerism
D007202:Indicators and Reagents; D003841:Deoxycytidine