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Title: Synthesis and conformational behavior of purine and pyrimidine beta-D-threo-hex-3'enopyranosyl nucleosides
Authors: Luyten, Ingrid ×
Herdewijn, Piet #
Issue Date: Jul-1996
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:52 issue:27 pages:9249-9262
Abstract: Based on the previous observation that anhydrohexitol nucleosides may exert antiviral activity, we have synthesized a series of beta-D-threo-hex-3'-enopyranosyl nucleosides starting from 1,5-anhydro-4,6-O-benzylidene-2-O-p-toluoyl-D-glucitol. These nucleosides adopt a predominant H-0(1) conformation with a pseudo axially oriented base moiety. This conformational behaviour can be explained by favorable pi-sigma* interactions, a gauche effect and hydrogen bond interactions. The alternative H-1(0) conformation is disfavored due to pseudo-1,3-diaxial interactions. Copyright (C) 1996 Elsevier Science Ltd
URI: 
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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