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A simple and efficient method for synthesis of 5-substituted 2′-deoxyuridine nucleosides using metal–halogen exchange reaction of 5-iodo-2′-deoxyuridine sodium salt

Author:
Aso, Mariko, Kaneko, Toshiyuki, Nakamura, Morihide, Koga, Noboru, Suemune, Hiroshi
Source:
Chemical communications 2003 no.9 pp. 1094-1095
ISSN:
1364-548X
Subject:
Lewis acids, chemical reactions, nucleosides, organosilicon compounds, regioselectivity, sodium
Abstract:
Treatment of the sodium salt of 2′-deoxy-3′, 5′-bis-O-(tert-butyldimethylsilyl)-5-iodouridine (3) with n-BuLi effected regioselective lithiation at the 5-position and the following reaction with various electrophiles afforded 5-substituted 2′-deoxyuridines including 1b, the precursor of stable spin-labeled 1a, in good yields.
Agid:
6573786