Title: 3'/5'-regioselectivity of introduction of the 9-fluorenylmethoxycarbonyl group to 2'-o-tetrahydropyran-2-yl-nucleosidesand 2'o-(4-methoxytetrahydropyran-4-yl)-nucleosides - useful intermediates for solid-phase-rna-synthesis
Authors: Lehmann, C ×
Xu, Yz
Christodoulou, C
Gait, Mj
Van Meervelt, Luc
Moore, M
Kennard, O #
Issue Date: Jan-1991
Publisher: Marcel dekker inc
Series Title: Nucleosides & nucleotides vol:10 issue:7 pages:1599-1614
Abstract: X-ray structure analysis of the more laevorotatory isomers of 2'-O-tetrahydropyranyl-4N-benzoylcytidine (4b) and of 2'-O-tetrahydropyranyluridine (5b) confirmed their chirality at the satellite anomeric centre C2'' to be S. The other diastereomers (4a resp. 5a) exhibited an unexpected reversal of 3'/5'-regio-selectivity when treated with 9-fluorenylmethoxycarbonyl chloride in pyridine. The X-ray crystallographic results form the basis for a mechanistic proposal.
ISSN: 0732-8311
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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