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Synthesis of mesoionic xanthine nucleosides
Authors:Richard A. Glennon  Ernst Schubert  R.Gerald Bass
Affiliation:Departments of Pharmaceutical Chemistry and Chemistry Virginia Commonwealth University, Richmond, VA 23298 U.S.A.
Abstract:The synthesis of the first examples of Class II mesoionic xanthine nucleosides is described. Tri-O-acetylribofuranosylaminothiazole is cyclized by condensation with bis (2,4,6-tri-chlorophenyl) malonate and the resultant product is de-protected to yield anhydro (8-β-D-ribofuranosyl-5-hydroxy-7-oxothiazolo [3,2-a] pyrimidinium hydroxide); the glucosyl derivative is prepared in a similar manner.
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