Synthesis of phosphonate analogs of nucleotides with a 2,5-dihydro-1,2-oxaphospholene carbon skeleton

Abstract

Electrophilic halogenation of substituted diethyl [4-(6-amino-9H-purin-9-yl)-3-methylbuta-1,2-dien-1-yl]phosphonates proceeded as a heterocyclization involving the phosphoryl oxygen atom of the phosphonate fragment. The reaction products were 9-[(2-ethoxy-4-halo-5-methyl-2-oxido-2,5-dihydro-1,2-oxaphosphol-5-yl)methyl]-9H-purin-6-amines, a new type of phosphonate analog of nucleotides.