5'-C-BRANCHED THYMIDINES - SYNTHESIS, STEREOCHEMISTRY, AND INCORPORATION INTO OLIGODEOXYNUCLEOTIDES

Thymidine was converted to its 5'(S)-epoxy derivative, which reacted w ith nucleophiles to give 5'(S)-C-aminomethyl-, 5'(S)-C-azidomethyl- 5' (S)-C-cyanomethyl-, and 5'(S)-C-methoxymethyl-thymidine with defined s tereochemistry. 5'-C-Allyl- and 5'-C-nitromethylthymidines were prepar ed from an aldehyde derivative. Stereochemistry of 5'-C-branched thymi dines was assigned with the help of NOE experiments. Four 5'-C-branche d thymidines were incorporated into oligodeoxynucleotides. Copyright ( C) 1996 Elsevier Science Ltd.