
TY  - JOUR
A1  - Johansen, O 
A1  - Marcuccio, SM 
A1  - Mau, AWH 
T1  - Nucleosides. III. Investigation of the Electrochemical Synthesis of N<sup>4</sup>, O<sup>5</sup>'-Diacetyl-2',3'-dideoxy-2',3'-didehydrocytidine
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1994
VL  - 47
IS  - 10
SP  - 1843
EP  - 1850
KW  - 
UR  - https://doi.org/10.1071/CH9941843 
N2  - The influence of the reaction conditions on the yield of N4,O5&#8242;-diacetyl-2&#8242;,3&#8242;-dideoxy-2&#8242;,3&#8242;-didehydrocytidine (3), by electrochemical synthesis from N4,O2&#8242;,O5&#8242;-triacetyl-3&#8242;-bromo-3&#8242;-deoxycytidine (2), has been studied in order to evaluate the potential of this reaction for synthesis on a larger scale. We have characterized the half-wave potentials of the precursor (2) and the product (3) by polarography under various conditions, and found that reduction in the base moiety can easily take place giving by-products. Furthermore, this reduction consumes protons leading to rapid solvolysis in protic solvents. We have demonstrated for the first time that (3) can be formed near quantitatively in both protic and aprotic solvents. The success of the synthesis of (3) as well as of other 2&#8242;,3&#8242;-dideoxy 2&#8242;,3&#8242;-didehydro nucleosides also depends to a large extent on how uniform the current density across the working electrode surface can be maintained during electrolysis. 
ER  -

