Facile Synthesis of 2′-Deoxyribofuranosides of Allopurinol and 4-Amino-1H-pyrazolo[3,4-d]pyrimidine via Phase-Transfer Glycosylation |
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Authors: | Frank Seela Herbert Steker |
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Institution: | Laboratorium fü Bioorganische Chemie, Fachbereich 13 – Organische Chemie, Universität Paderborn, Warburgerstr. 100, D–4790 Paderborn |
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Abstract: | Phase-transfer glycosylation of 4-methoxy-1H-pyrazolo3,4-d]pyrimidine with the 2-deoxyribofuranosyl chloride 9 formed the N(1)-β-nucleoside 10a as main product (39%). As by-products the α-D -anomer 11a (7%) and the N(2)-isomer 12a (18%) were isolated. Assignment of these isomers was made on the basis of their 1H- and 13C-NMR spectra. Removal of the sugar-protecting groups yielded the 4-methoxy-nucleosides 10b, 11b , and 12b , respectively. Nucleophilic displacement of the 4-MeO-group gave the 2-deoxyribofuranosides 1–4 of allopurinol and 4-amino-1H-pyrazolo3,4-d]pyrimidine. |
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