Studies on Nucleosides and Nucleotides. LXXXVII. Purine Cyclonucleosides. XLII. Synthesis of 2′-Deoxy-2′-fluoroguanosine

Abstract

2′-Deoxy-2′-fluoroguanosine (VII) was synthesized starting from 8,2′-anhydro-8-oxy-9-β-D-arabinofuranosylguanine (8,2′-O-cycloguanosine) (I). Compound I was protected at 2-NH2 with an isobutyryl group and at 3′- and 5′-OH with tetrahydrofuranyl groups. The protected compound III was derivatized to the arabino nucleoside V and thence converted to VII by treatment with trifluoromethanesulfonyl chloride and tetra-n-butylammonium fluoride. The resulting 2′-deoxy-2′-fluoroguanosine showed a 3′-endo favored conformation. © 1981, The Pharmaceutical Society of Japan. All rights reserved.