Darstellung und Charakterisierung von Trifluormethylchalkogenyl substituierten Nucleosiden

DOI: 10.1016/S0022-1139(00)80181-5

Source and publish data:

Journal of Fluorine Chemistry p. 55 - 76 (1992)

Update date:2022-09-26

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Authors:

Haas, Alois

Lieb, Max

Steffens, Bernd

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Article abstract of DOI:10.1016/S0022-1139(00)80181-5

5-Trifluoromethylchalcogenyl-substituted 2'-desoxy-uridines and -cytidines have been synthesized from 2-desoxy-3,5-di-O-(4-methylbenzoyl)-α-D-ribofuranosyl chloride and CF3E-substituted (E=S, SO2, Se) silylated pyrimidines by a modified Hilbert-Johnson reaction.By choosing proper reaction conditions β-anomers may be obtained as the main product.The nucleoside are deprotected by basic transesterification with NH3/CH3OH.After recrystallization from H2O/C2H5OH, 5-trifluoromethylchalcogenyl-2'-desoxynucleosides are formed in good yields.Systematically studiedsubstitution reactions on 5-trifluoromethylsulfanyl-2'-desoxyuridine are described. 5-Trifluoromethylsulfanyl-2',3'-didesoxyuridine is formed by Barton desoxygenation.For the first time, CF3S substitutions at the sugar part of a nucleoside are described.

Full text of DOI:10.1016/S0022-1139(00)80181-5

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