Title: Synthesis of 4-deoxy-4-C-hydroxymethyl-alpha-L-lyxopyranosyl thymine
Authors: Doboszewski, Bogdan ×
Herdewijn, Piet #
Issue Date: 1996
Publisher: M. Dekker
Series Title: Nucleosides & Nucleotides vol:15 issue:9 pages:1495-1518
Abstract: The synthesis of 1-[4-deoxy-4-C-hydroxymethyl-alpha-L-lyxopyranosy]thymine has been accomplished by two synthetic routes both starting from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside. The first route makes use of a ring opening, ring closure reaction sequence to increase the proportion of the desired L-isomers. The second route utilizes the soft nucleophilic character of malonyl anions and ozonolytic cleavage of enol ether to introduce the branched chain. The newly obtained pyranosyl nucleoside obtains a C-4(1) conformation with an equatorially oriented thymine moiety.
ISSN: 0732-8311
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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