Issue 20, 2006

Sulfanyl radical promoted C4′–C5′ bond scission of 5′-oxo-3′,4′-didehydro-2′,3′-dideoxynucleosides

Abstract

Treatment of C5′-aldehydes 4a,b under mildly basic conditions leads to the formation of 3′,4′-didehydroaldehydes 1a,b and furfural 2. Sulfanyl radical addition to 1a,b eventually gives rise to the lactones 11a,b through C4′–C5′ bond scission of the 1,2-dioxetane intermediates 10a,b.

Graphical abstract: Sulfanyl radical promoted C4′–C5′ bond scission of 5′-oxo-3′,4′-didehydro-2′,3′-dideoxynucleosides

Supplementary files

Article information

Article type
Communication
Submitted
12 Jul 2006
Accepted
04 Sep 2006
First published
12 Sep 2006

Org. Biomol. Chem., 2006,4, 3754-3756

Sulfanyl radical promoted C4′–C5′ bond scission of 5′-oxo-3′,4′-didehydro-2′,3′-dideoxynucleosides

M. L. Navacchia and P. C. Montevecchi, Org. Biomol. Chem., 2006, 4, 3754 DOI: 10.1039/B609995E

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