A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives.
A seven-step synthesis of 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose, a versatile intermediate in the synthesis of chemotherapeutically important nucleosides, was achieved from 1,2:5,6-di-O-isopropylidene-3-O-tosyl-alpha-D-allofuranose. The crucial steps were the fluorination by use of potassium fluoride in acetamide and the conversion of 6-O-benzoyl-3-deoxy-3-fluoro-D-glucofuranose into 5-O-benzoyl-2-deoxy-2-fluoro-3-O-formyl-D-arabinofuranose by periodate oxidation. Also described is the synthesis of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine. This procedure affords good overall yields of products without formation of undesirable, isomeric intermediates and is suitable for large-scale preparations.
D001089:Arabinose / Q000031:analogs & derivatives*; D002855:Chromatography, Thin Layer; D003460:Crystallization; D003561:Cytarabine / Q000031:analogs & derivatives; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D005461:Fluorine; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009904:Optical Rotation
D003837:Deoxy Sugars; D003561:Cytarabine; D005461:Fluorine; D001089:Arabinose