Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 4, Issue 11, Pages 2278-2284Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b604010a
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An expeditious and highly efficient single-step methodology for the introduction of a phenylalanine moiety into position 8 and 6 of the purine scaffold was developed based on aqueous-phase Pd-catalysed Suzuki - Miyaura cross-coupling reactions of unprotected 4-boronophenylalanine with 8-bromo- or 6-chloropurines. The scope of the methodology was demonstrated by syntheses of unprotected (adenin-8-yl) phenylalanine base, nucleosides, nucleotides and nucleoside triphosphates as well as (purin-6-yl) phenylalanine base and nucleosides. All these products were obtained in high yields and in optically pure form.
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