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Communication | Regular issue | Vol 23, No. 10, 1985, pp.2521-2524
Published online, 1st January, 1970
DOI: 10.3987/R-1985-10-2521
■ Synthesis of the β-D-Deoxyribofuranoside of 6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one — A New Isoster of 2’-Deoxyguanosine

Frank Seela* and Herbert Steker

*Laboratorium für Bioorganische Chemie, Fachbreich Chemie, Universität Paderborn, D-4790, Paderborn, Germany

Abstract

6-Amino-1-(2-deaxy-β-O-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (8) has been synthesized via regio- and diastereo-selective phase-transfer glycosylation of 6-amino-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (4) with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (5). Compound 4 was obtained from 2-amino-4,6-dichloro-5-pyrimidinecarboxaldehyde (2a). Hydrolysis experiments under acidic conditions showed that the N-glycosylic bond of 8 is more labile than that of 2‘-deaxyguanosine.