Preparation of 1-(3-C-(propa-1,2-dienyl)D-ribo-pentofuranosyl)uracil, an allenic nucleoside

Authors
Dauvergne, J Burger, A Biellmann, JF
Citation
J. Dauvergne et al., Preparation of 1-(3-C-(propa-1,2-dienyl)D-ribo-pentofuranosyl)uracil, an allenic nucleoside, NUCLEOS NUC, 20(10-11), 2001, pp. 1775-1781
Citations number
10
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
ISSN journal
15257770 → ACNP
Volume
20
Issue
10-11
Year of publication
2001
Pages
1775 - 1781
Database
ISI
SICI code
1525-7770(2001)20:10-11<1775:PO1AA>2.0.ZU;2-2
Abstract
The Crabbe reaction was extended to the preparation of C-3'-allenyluridine. The effects of solvent and protecting group on the reaction were studied. The conversion in refluxing dioxan of disilyl either 3 proceeds to the corr esponding allenic nucleoside 7; whereas, in refluxing THF the Mannich base 5 was obtained. Fully deprotected Mannich base and allenic uridines 6 and 9 were tested for their antitumor activity.