Synthesis of C-Nucleosides Related to Adenosine as Potential Antimalarials.
Annual summary rept. no. 4, 1 Feb 73-31 Jan 74,
OREGON GRADUATE CENTER BEAVERTON
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A synthetic study of C-nucleoside analogs of adenosine for evaluation as potential antimalarials was undertaken. Strategically the synthetic route chosen because of its generality involves coupling of preformed nitrogen heterocyclic base and carbohydrate derivatives using an organometallic coupling reaction to effect the key glycosidic linkage. This synthetic sequence can be visualized as involving four discrete stages for investigation preparation of the precursor base and carbohydrate components protection of sensitive functional groups on the heterocyclic base coupling of the base and carbohydrate precursors to form a C-nucleoside and elaboration of the desired base and carbohydrate substituents. The result of these investigations has been the preparation in fifteen synthetic steps of a C-nucleoside, 3-ribofuranosylpyrazolo4,3-dpyrimidine. Modified author abstract