A stereoselective synthesis of 9-(3-O-benzyl-5-O-tetrahydropyranyl-β-d-arabinofuranosyl)adenine, a potentially useful intermediate for ribonucleoside synthesis

A novel synthesis for preparing 9-(3-O-benzyl-5-O-tetrahydropyranyl-β-d-arabinofuranosyl)adenine () has been developed which does not require sub zero temperatures or exotic reagents. A key step in this synthesis is the selective protection of the 3′-OH of ara-A with a benzyl group. The 5′-OH is then selectively protected with DHP to yield , a potentially useful intermediate. A synthesis of 9-(2,3-dideoxy-2-fluoro-β-d-threo-pentofuranosyl)adenine (, FddA), an anti-viral compound, is given to illustrate the utility of this new approach.