Helvetica Chimica Acta p. 1818 - 1836 (2007)
Update date:2022-08-03
Topics:
Sivets, Grigorii G.
Kalinichenko, Elena N.
Mikhailopulo, Igor A.
Convergent syntheses of the 9-(3-X-2,3-dideoxy-2-fluoro-β-D- ribofuranosyl)adenines 5 (X = N3) and 7 (X = NH2), as well as of their respective α-anomers 6 and 8, are described, using methyl 2-azido-5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-ribofuranoside (4) as glycosylating agent. Methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-β-D- ribofuranoside (12) was prepared starting from two precursors, and coupled with silylated N6-benzoyladenine to afford, after deprotection, 2′,3′-dideoxy-2′,3′-difluoroadenosine (13). Condensation of 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranose (14) with silylated N2-palmitoylguanine gave, after chromatographic separation and deacylation, the N7-β-anomer 17 as the main product, along with 2′-deoxy-2′-fluoroguanosine (15) and its N9-α- anomer 16 in a ratio of ca. 42:24:10. An in-depth conformational analysis of a number of 2,3-dideoxy-2-fluoro-3-X-D-ribofuranosides (X = F, N3, NH2, H) as well as of purine and pyrimidine 2-deoxy-2-fluoro-D- ribofuranosyl nucleosides was performed using the PSEUROT (version 6.3) software in combination with NMR studies.
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