8-Bromo-2'-deoxyadenosine → HCID 178508654, compound

Participants

Reaction Steps

The starting compound for the synthesis of VIII was 8-bromo-2'-deoxyadenosine which was prepared by bromination of the corresponding deoxynucleoside. This starting compound was first converted to its azido derivative and then subjected to the deoxygenation procedure. During the nBu3SnH/AIBN step, reduction of the azido group occurred concomitantly with the deoxygenation. In a related procedure, 8-bromo-2'-deoxyadenosine was converted to the corresponding 8-methoxy compound and then deoxygenated to 2',3'-dideoxy-8-methoxyadenosine (IX). 2',3'-Dideoxy-8-thiomethyl- adenoxine (XI) can be similarly prepared from 8-thiomethyl- 2'-deoxyadenosine. Compound IX can be demethylated to give 2',3'-dideoxy-8-hydroxyadenosine (X).

Provenance & Evidence