The first investigation of borane-unsaturated nucleoside reaction system

A novel synthetic approach is presented, involving unsaturated nucleoside hydroboration, with protected stavudine catalytically boronated with pinacolborane to several pinacolborane derivatives of stavudine or 2',3'-dideoxythymidine. The products were converted to much more stable trifluoroborate derivatives that may be considered trifluoroboron analogues of nucleoside phosphates. The post-reaction mixture contained four isomers, being products of catalytic hydroboration, and two isomers, resulting from dehydrogenative borylation, each containing unsaturated 2',3'-moiety. The new compounds were analyzed with NMR and LDI-HRMS methods.

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