Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives ("Naked sugars") as synthetic intermediates. Part XXII. Stereoselective synthesis of (1R)-1-C-(6-amino-7H-purin-8-yl)-1,4-anhydro-2,3-dideoxy-3-fluoro-D-erythro-pentitol

Pechy, Peter; Gasparini, Fabrizio; Vogel, Pierre

doi:10.1055/s-1992-21455

research article

Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives ("Naked sugars") as synthetic intermediates. Part XXII. Stereoselective synthesis of (1R)-1-C-(6-amino-7H-purin-8-yl)-1,4-anhydro-2,3-dideoxy-3-fluoro-D-erythro-pentitol

Pechy, Peter

•

Gasparini, Fabrizio

•

Vogel, Pierre

1992

Synlett

The "naked sugar" (+)-(1R,2S,4R)-2-cyano-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl (1S)-camphanate [(+)-3] (Diels-Alder adduct of furan with 1-cyanovinyl (1S)-camphanate) was converted into (1R)-1-C-(6-amino-7H-purin-8-yl)-1,4-anhydro-2,3-dideoxy-3-fluoro-D-eryt hro-pentitol [(+)-2] in nine synthetic steps and 12% overall yield.