Synthesis study of 3'-alpha-fluoro-2',3'-dideoxyguanosine.
A synthetic method was established for 3'-alpha-fluoro-2','3-dideoxyguanosine 1 from guanosine 2 in 27% overall yield and 6 steps. A byproduct 6a of fluorination was identified by NMR studies, its presence strongly supporting our supposition that the fluorination itself proceeded via a bromonium cation.
Torii
Takayoshi
T
AminoScience Laboratories, Ajinomoto Co., Inc., Kawasaki, Japan.
Onishi
Tomoyuki
T
Tanji
Shigehisa
S
Izawa
Kunisuke
K
D019380:Anti-HIV Agents / Q000494:pharmacology; D000998:Antiviral Agents / Q000494:pharmacology; D002412:Cations; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D005461:Fluorine / Q000737:chemistry; D006151:Guanosine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods*; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D002412:Cations; D015224:Dideoxynucleosides; D009841:Oligonucleotides; D006151:Guanosine; D005461:Fluorine; C055315:3'-fluoro-2',3'-dideoxyguanosine