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Synthesis 1988; 1988(9): 670-674
DOI: 10.1055/s-1988-27667
DOI: 10.1055/s-1988-27667
paper
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Synthesis of 6-Substituted 7-Carbapurine 2′,3′-Dideoxynucleosides: Solid-Liquid Phase-Transfer Glycosylation of 4-Chloropyrrolo[2,3-d]pyrimidine and Deoxygenation of its 2′-Deoxyribofuranoside
Further Information
Publication History
Publication Date:
18 September 2002 (online)
Several 4-substituted pyrrolo[2,3-d]pyrimidine 2′, 3′-dideoxyribofuranosides including 2′,3′-dideoxytubercidin (10) and 2′,3′-dideoxy-7-carbainosine (12) are prepared from 4-chloro-7-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-7H-pyrrolo [2,3-d]pyrimidine (8). Compound 8 is obtained from the corresponding 4-chloro-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo [2,3-d]pyrimidine (4a) via Barton-deoxygenation. Its protected precursor 3 is accessible in 81% yield by solid-liquid phase-transfer glycosylation.