Synthesis of a 3′-Fluoro-3′-deoxytetrose Adenine Phosphonate

5 years ago

Synthesis of a 3′-Fluoro-3′-deoxytetrose Adenine Phosphonate

Piet Herdewijn, Steven De Jonghe, Swarup De

A new synthetic route to a 3′-fluoro-3′-deoxytetrose adenine phosphonate has been developed. The synthesis starts from l-xylose and key steps include the stereospecific introduction of the phosphonomethoxy group and adenine. In addition, a regioselective fluorination reaction allows access to the desired 3′-fluoro-3′-deoxytetrose moiety. This methodology allows the straightforward synthesis of a 3′-fluoro-3′-deoxytetrose adenine phosphonate and can be expanded toward the synthesis of other types of 3′-fluoro nucleoside phosphonates.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01482

DOI: 10.1021/acs.joc.7b01482