Synthesis of (Z)- and (E)-N 9-(4-hydroxy-1-buten-1-yl)adenine - new unsaturated analogues of adenosine

Abstract

The title 1-butenols 5b and 6b were obtained by isomerization of 2-butenols 2b and 3b catalyzed by potassium tert-butoxide ( tBuOK) in dimethylformamide ( DMF). Reaction of Z-olefin 2b was highly stereoselective to give E-isomer 5b whereas E-olefin 3b afforded predominantly Z-isomer 6b. Compounds 5b and 6b are substrates for adenosine deaminase, 6b being substantially less active than 5b.