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Title: Synthesis of (E)-3 '-Phosphonoalkenyl Modified Nucleoside Phosphonates via a Highly Stereoselective Olefin Cross-Metathesis Reaction
Authors: Huang, Qiuya
Herdewijn, Piet # ×
Issue Date: May-2011
Publisher: American Chemical Society
Series Title: Journal of Organic Chemistry vol:76 issue:10 pages:3742-3753
Abstract: The synthesis of (E)-3'-phosphonoalkenyl and 3'-phosphonoalkyl modified nucleoside analogues with a beta-D-erythrofuranose moiety is reported. The highly stereoselective olefin cross-metathesis reaction was applied to introduce the phosphonoalkenyl group at the 3'-position of the sugar moiety with absolute (E)-selectivity. The 3',6'-cyclomonophosphonic acids of 3'-phosphonoethyl-beta-D-erythrofuranosyl nucleosides were synthesized via a dehydrative intramolecular cyclization reaction. None of the synthesized compounds shows significant in vitro activity against HIV, HCV, and RSV.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
Interface Valorization Platform (IVAP) (-)
× corresponding author
# (joint) last author

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