Title: Stereocontrolled synthesis of phosphonate derivatives of tetrahydro-and dihyrdo-2H-pyranyl nucleosides: The selectivity of the Ferrier rearrangement.
Authors: Pérez-Pérez, MJ ×
Doboszewski, Bogdan
Rozenski, Jef
Herdewijn, Piet #
Issue Date: Apr-1995
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron-asymmetry vol:6 issue:4 pages:973-984
Abstract: Phosphonate derivatives of 2,5-cis substituted tetrahydro- and dihydro-2H-pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4-trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5-cis-dihydro-2H-pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5-cis-dihydro-2H-pyranyl nucleosides.
ISSN: 0957-4166
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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