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A synthesis of cytidine‐5‐ 3 H
Author(s) -
van Zanten B.,
den Hollander W.
Publication year - 1966
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590020309
Subject(s) - cytidine , toluene , benzene , chemistry , solvent , salt (chemistry) , tritium , medicinal chemistry , organic chemistry , physics , enzyme , nuclear physics
Cytidine‐5‐ 3 H was synthesized, by the incorporation of 1.1‐diethoxy 2‐cyanoethane‐2‐ 3 H (cyanoacetal‐2‐ 3 H), using an adaption of the procedure described by Codington ( 1 ) for the synthesis of cytidine‐2‐ 14 C. The final step in this procedure was the coupling of the mercuric compound of the base with the blocked chloro‐sugar in a toluene‐benzene solvent. The fact that this reaction can be used indicates that mercuric‐salt catalyzed hydrogen exchange between benzene‐toluene solvent and nucleoside, as described by LePage and Junga ( 2 ), does not occur with cytidine at least at the 5‐position. Furthermore the present investigation shows that dimethyl acetamide is an excellent aprotic solvent and can be used as such for reactions involving exchange of labile tritium under alkaline conditions.