693253-03-1Relevant articles and documents
A stereoselective synthesis of 9-(3-O-benzyl-5-O-tetrahydropyranyl-β- D-arabinofuranosyl)adenine, a potentially useful intermediate for ribonucleoside synthesis
Woltermann, Christopher J.,Lapin, Yuri A.,Kunnen, Kevin B.,Tueting, David R.,Sanchez, Ignacio H.
, p. 3445 - 3449 (2004)
A novel synthesis for preparing 9-(3-O-benzyl-5-O-tetrahydropyranyl-β- D-arabinofuranosyl)adenine (6) 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 6, a potentially useful intermediate. A synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo- pentofuranosyl)adenine (1, FddA), an anti-viral compound, is given to illustrate the utility of this new approach.