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- W1971102271 abstract "Various 2,3-dideoxy-2,2-difluoro-l-glycero-pentofuranosyl nucleosides were synthesized via the key intermediate, 5-O-benzoyl-2,3-dideoxy-2,2-difluoro-l-glycero-pentofuranose (6). 2,3-O-Isopropylidene-l-glyceraldehyde was coupled with ethyl bromodifluoroacetate under Reformatsky conditions to obtain the diastereomeric mixture of ethyl (4S)-3-hydroxy-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro propionate (1). Treatment of compound 1 with carbon disulfide, sodium hydride and methyl iodide followed by reduction afforded ethyl (4S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro propionate (3). Compound 3 was treated with 5% HCl in ethanol, followed by refluxing in benzene under Dean–Stark conditions, to afford the lactone 4. The compound 4 was protected and reduced to afford the key intermediate 6. For the synthesis of pyrimidine derivatives 8–21, compound 6 was converted to the mesylate 7 and condensed with various silyl protected pyrimidine bases. The inosine and adenine derivatives 38–41 were obtained from compound 6 and 6-chloropurine using standard procedures. Compounds 22–35 and 38–41 were evaluated for their antiviral activity against HIV-1, HBV, HSV-1 and HSV-2, and for cellular toxicity. None of the synthesized compounds showed any significant activity or toxicity. Single-crystal X-ray structure of 1-(2,3-dideoxy-2,2-difluoro-β-l-glycero-pentofuranosyl)-5-iodocytosine (34) suggested a 2′-exo/3′-endo conformation for the carbohydrate moiety." @default.
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- W1971102271 date "1998-01-01" @default.
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- W1971102271 title "Synthesis of 2,3-dideoxy-2,2-difluoro-l-glycero-pentofuranosyl nucleosides" @default.
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- W1971102271 doi "https://doi.org/10.1016/s0008-6215(97)00275-9" @default.
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