Preparation of carbocyclic phosphonate nucleosides

✍ Scribed by Gerhard Jähne; Armin Müller; Herbert Kroha; Manfred Rösner; Otto Holzhäuser; Christoph Meichsner; Matthias Helsberg; Irvin Winkler; Günther Rieß

• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 305 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79086-1

✦ Synopsis

kbstract:. A versatile and high-yielding synthesis of racemic carbocyclic ohosphonate nucleosides of adenine, hypoxanthine, guanine, cytosine, uracil, and O~ymine has been developed. These newly prepared compounds are isosteric (and isoelectronic) with (carbo)cyclic 2',3'-dideoxy-and 2;3'dideoxy-2',3'-didehydronucleoside monophos~ates.

Dideoxynucleosides like Y-azido-Y-deoxythymidiue (zidovudine) and 2',Y-dideoxyinosine (didanosine) are cturently the only licensed drugs for the anti-HIV treatment of AIDS patients [I]. Members of the dideoxy class of compounds, however, are perceived to have a number of disadvantages, including toxicity and lability of the glycosidic bond to acidic or enzymic cstalysis . In an attempt to overeon~ some of these drawbacks, dideoxy-and dideoxy-didehydronucleoside analogues in which