- Simple Method for the Synthesis of 5-Substituted 2',5'-Anhydro-2',5'-dideoxy-1-β-D-arabinofuranosyluracils
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Reaction of 5-substituted 2',5'-dichloro-2',5'-dideoxyuridines (1) with methanolic sodium hydroxide under reflux afforded the corresponding 5-substituted 2',5'-anhydro-2',5'-dideoxy-1-β-D-arabinofuranosyluracils (2) in high yields.
- Hirota, Kosaku,Kitade, Yukio,Tomishi, Tetsuo,Maki, Yoshifumi
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- PREPARATION OF THE 1-(2,5-ANHYDRO-β-D-ARABINOFURANOSYL) DERIVATIVE OF CYTOSINE AND URACIL AND THEIR CLEAVAGE WITH HYDROGEN BROMIDE
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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
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p. 2961 - 2968
(2007/10/02)
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