title: Synthesis of 8-(omega-Hydroxyalkyl)-, 8-(omega-hydroxyalk-1-enyl)-, and 8-(omega-hydroxyalk-1-ynyl)adenines using the tert-butyldimethylsilyloxymethyl group, a new and versatile protecting group of adenine.
abstract: The synthesis of 12 analogues of adenine substituted at C-8 by an omega-hydroxyalkyl, omega-hydroxyalk-1-enyl, or omega-hydroxyalk-1-ynyl chain of various length has been carried out in five or six steps starting from adenine. The analogues were obtained using a new protecting group of adenine, the tert-butyldimethylsilyloxymethyl group. 9-tert-Butyldimethylsilyloxymethyl-adenine is more soluble than adenine in organic solvents. It was prepared regiospecificaly in two steps from adenine and was amenable to C-8 iodination under basic conditions and to subsequent introduction of the various carbon chains at C-8 by palladium-catalyzed cross-coupling reactions (Stille or Sonogashira). The protecting group was removed under acidic conditions, thus demonstrating its versatility.
authors.affiliation: Laboratoire de Chimie Organique Biologique, UMR 7509, Faculté de Chimie, Université Louis Pasteur, 1 rue Blaise Pascal, 67008 Strasbourg Cedex, France.
authors.forename: P
authors.initials: P
authors.lastname: Lang
authors.forename: G
authors.initials: G
authors.lastname: Magnin
authors.forename: G
authors.initials: G
authors.lastname: Mathis
authors.forename: A
authors.initials: A
authors.lastname: Burger
authors.forename: J F
authors.initials: JF
authors.lastname: Biellmann
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*
chemical_list: D000998:Antiviral Agents; D000225:Adenine