The first investigation of borane-unsaturated nucleoside reaction system
Joanna Nizioł, Wojciech Rode and Tomasz Ruman
Rzeszów University of Technology, Faculty of Chemistry, Bioorganic Chemistry Laboratory, 6 Powstańców Warszawy Ave. 35-959 Rzeszów, Poland
Nencki Institute of Experimental Biology, 3 Pasteur Street, 02-093 Warsaw, Poland
Abstract: 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.
Keywords: BNCT; boron nucleoside; boron nucleotide; dehydrogenative borylation; hydroboration; NMR; nucleoside trifluoroborate. © 2015 ACG Publications. All rights reserved. |