Preparation of 4′-benzenesulfonyl-3′-deoxythymidine and its reaction with organoaluminum and organosilicon reagents

The 4′-benzenesulfonyl derivative of 3′-deoxythymidine was prepared from 3′-deoxythymidine-5′-aldehyde. The 4′-benzenesulfonyl leaving group undergoes a nucleophilic substitution with organoaluminum and organosilicon reagents to furnish a variety of 4′-substituted (Me, Et, i-Bu, trimethylsilylethynyl, CH2CHCH2, CN, N3) analogues.

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