Synthesis of 2',3'-dideoxy-3'-fluoro-L-ribonucleosides as potential antiviral agents from D-sorbitol.
2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2,3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-alpha-L-cytidine showed a moderate anti-HBV activity.
Chun
B K
BK
Department of Pharmaceutical and Biomedical Sciences, College of Pharmacy, The University of Georgia, Athens 30602, USA.
Schinazi
R F
RF
Cheng
Y C
YC
Chu
C K
CK
D000998:Antiviral Agents / Q000138:chemical synthesis*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D005461:Fluorine; D006515:Hepatitis B virus / Q000187:drug effects; D013012:Sorbitol / Q000737:chemistry*; D013237:Stereoisomerism
C418763:2',3'-dideoxy-3'-fluorocytidine; D000998:Antiviral Agents; D015224:Dideoxynucleosides; D003841:Deoxycytidine; D005461:Fluorine; D013012:Sorbitol