Antiviral nucleosides. A stereospecific, total synthesis of 2'-fluoro-2'-deoxy-. beta.-D-arabinofuranosyl nucleosides

…, SP Brundidge, DA Benigni, C Sapino Jr

Index: Howell, Henry G.; Brodfuehrer, Paul R.; Brundidge, Steven P.; Benigni, Daniel A.; Sapino, Chester Journal of Organic Chemistry, 1988 , vol. 53, p. 85 - 88

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Citation Number: 111

Abstract

8a-d report now describes the coupling of 6 (via the 1-a-bromo 7) with silylated pyrimidines which completed a stereospecific, high-yield route to the known5 blocked, P-nucleosides 8a- d (Scheme 11). When the bromination method reported by Fox5 was employed with 6, a single bromo anomer was obtained in quantitative yield. The anomeric proton of 7 was assigned to a doublet at 6.7 ppm (J= 11.9 Hz) in the NMR spectrum; however, no coupling ...