Synthesis of carbocyclic 2′3′-dideoxy-2′-fluoro-3′-C-hydroxymethyl nucleoside analogues as potential inhibitors of HIV and HSV

✍ Scribed by Johanna Wachtmeister; Classon Björn; Samuelsson Bertil; Ingemar Kvarnström

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 872 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01103-9

✦ Synopsis

The synthesis of four isomerically pure tluoro-carbocyclic adenosine and guanosine analogues is described. The 3S,4S-bis(r-butyldiphenylsilyloxymethyl)-2-fluoropentan-l-o~ derivatives 22, 23, 24 and 25 synthesised from enantiomerically pure 3S,4S-bis(t-butyldiphenylsilyloxymethyl)-cyclopentanone (18) were coupled with chloropurines using the Mitsunobu procedure to give 10, 11, 12, 14 and 16 or converted to their corresponding l-amino derivatives, from which the fluoro-carbocyclic guanosine analogues 13.15 and 17 were prepared. Compounds lo-17 were evaluated as potential anti-viral agents but were found to be inactive.