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Abstract Synthesis of 2ʹ-deoxy-5-fluoromethyluridine (dUCH2F) and 2ʹ-deoxy-5-difluoromethyluridine (dUCHF2) phosphoramidites was achieved. The obtained phosphoramidites were efficiently incorporated into oligonucleotides (ONs), and their post-synthetic modification was examined. In the case of… Click to show full abstract
Abstract Synthesis of 2ʹ-deoxy-5-fluoromethyluridine (dUCH2F) and 2ʹ-deoxy-5-difluoromethyluridine (dUCHF2) phosphoramidites was achieved. The obtained phosphoramidites were efficiently incorporated into oligonucleotides (ONs), and their post-synthetic modification was examined. In the case of dUCH2F-containing ONs, substitution of the fluorine atom with methoxy, hydroxy and amine groups was successful. Moreover, the difluoromethyl group of dUCHF2 in the ONs could be converted to a formyl, oxime, or hydrazone by treatment with the corresponding nucleophile.
Journal Title: Tetrahedron
Year Published: 2021
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