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Issue 1, 2003
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Studies on 2′-α-C-carboxyalkyl nucleosides and their application to a stereocontrolled nucleobase exchange process

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Abstract

The ability of 2′-α-C-carboxyalkyl nucleosides to undergo an unusual two-step stereocontrolled nucleobase exchange process has been investigated. Upon silylation a protected 2′-deoxy-2′-α-C-(carboxymethyl)uridine derivative can undergo intramolecular displacement of the uracil base, by the 2′-carboxylic acid group, to form a pentofuranosyl γ-lactone. Under identical conditions the homologous 2′-deoxy-2′-α-C-(carboxyethyl)uridine derivative does not yield the corresponding δ-lactone, but undergoes elimination of uracil to give the corresponding glycal. The pentofuranosyl γ-lactone is a good substrate for nucleoside synthesis by the Vorbrüggen procedures and undergoes completely stereoselective ring opening with either pyrimidine or purine silylated nucleobases to give novel 2′-C-carboxymethyl β-nucleosides in moderate to high yield.

Graphical abstract: Studies on 2′-α-C-carboxyalkyl nucleosides and their application to a stereocontrolled nucleobase exchange process

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Publication details

The article was received on 09 Sep 2002, accepted on 15 Oct 2002 and first published on 26 Nov 2002


Article type: Paper
DOI: 10.1039/B208786N
Org. Biomol. Chem., 2003,1, 123-128

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    Studies on 2′-α-C-carboxyalkyl nucleosides and their application to a stereocontrolled nucleobase exchange process

    V. Fehring, S. Knights, M. Chan, I. A. O'Neil and R. Cosstick, Org. Biomol. Chem., 2003, 1, 123
    DOI: 10.1039/B208786N

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