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Addition of Grignard Reagents to 4-O-TPS pyrimidine Nucleosides: Synthesis of 6-substituted 5,6-dihydropyrimidine nucleoside derivatives

✍ Scribed by Norbert Bischofberger

Book ID: 104229688
Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 277 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)99536-4

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✦ Synopsis

Methyl magnesium chloride, vinyl magnesium chloride and acetylides were found to add to 4-Otriisopropylphenylsulphonyl (TPS) uridine and thymidine derivatives at the 6-position leading to 6-substituted-3,6-dihydro-4-0-TPS pyrimidine nucleosides. Reaction with phenyl magnesium chloride resulted in addition at both the 6-and the 4positions.

Nucleoside and nucleotide derivatives exhibit a wide range of biological effects, most notably antiviral and anticancer activities. Among the large number of nucleoside analogs prepared as potential agents against viral diseases and cancers, 6-C-substituted pyrimidine nucleosides have attracted relatively scant attention,' which may be due to their

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