- PREPARATION OF THE 1-(2,5-ANHYDRO-β-D-ARABINOFURANOSYL) DERIVATIVE OF CYTOSINE AND URACIL AND THEIR CLEAVAGE WITH HYDROGEN BROMIDE
-
Anhydronucleoside Ia was prepared from chloroarabinofuranoxylcytosine IIIc or from 2,2'-anhydro-1-(5-chloro-5-deoxy-β-D-arabinofuranosyl)cytosine by the action of a strongly basic ion exchanger.The anhydro derivative IIa was prepared from 2,2'-anhydro-1-(5-chloro-5-deoxy-β-D-arabinofuranosyl)uracil by treatment with aqueous solution of sodium hydroxide.The action of hydrogen bromide in dimethylformamide on 2',5'-anhydronucleosides Ia and IIa leads both to the cleavage of the anhydro bond under formation of the 5'-bromo derivatives IIIa and IVa and to the cleavage of nucleosidic bond.In case of uracil derivative IIa, the α-arabinofuranosyl derivative V was also isolated after preceding acetylation.For unambiguous proof of the structure, an alternative synthesis of compound V was performed.
- Hrebabecky, Hubert,Brokes, Josef,Beranek, Jiri
-
p. 2961 - 2968
(2007/10/02)
-