′-Deoxy-2 ′-fluoro-â-D-arabinonucleosides : Modified DNA Constituents with an Unusually Rigid Sugar N-Conformation

Abstract

The nucleobase anion glycosylation of 3-bromo-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine (6) with 3,5-di-O-benzoyl-2-deoxy-2-fluoro-R-D-arabinofuranosyl bromide (5) furnished the protected N1-â-D-nucleosides 7 (60%) and 8 (ca. 2%) along with the N2-â-D-regioisomer 9 (9%). Debenzoylation of compounds 7 and 9 yielded the nucleosides 10 (81%) and 11 (76… (More)

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