6-O-(Pentafluorophenyl)-2'-deoxyguanosine: A Versatile Synthon for Nucleoside and Oligonucleotide Synthesis

Article abstract of DOI:10.1021/jo00051a051

The 6-O-(pentafluorophenyl)-2'-deoxyguanosine derivative 2a can be used to generate in high yield 6-O-methyl-2'-deoxyguanosine, 2,6-diamino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine, and related derivatives.Further, after appropriate protection and derivatization, 2a can be incorporated into oligonucleotides and there used for postsynthetic oligonucleotide modification.This approach is particularly useful for preparation of oligonucleotides containing 2,6-diaminopurine residues or their 6-alkylamino derivatives.In addition, reaction of 2a, or oligonucleotides containing it, with 4-(dimethylamino)pyridine (DMAP) gives a fluorescent guanine-DMAP adduct.