5'-C-branched thymidines: Synthesis, stereochemistry, and incorporation into oligodeoxynucleotides

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