title: Synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde: application to the synthesis of potent adenosine A(2A) and A(3) receptor agonist.
abstract: Synthesis of potent adenosine A(2A) and A(3) receptor agonist from the modification of adenosine-5'-N-ethylcarboxamide (NECA) has been reported. Diastereoisomer possessing an (R) 3,4-dihydro-2H-pyranyl (DHP) moiety exhibited the highest affinity at the A(2A) and A(3) receptors. The key steps involve the synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde (7), which was obtained through the enzyme catalyzed kinetic resolution of (±)-2-acetoxymethyl-3,4-dihydro-2H-pyran (5).
authors.affiliation: Inotek Pharmaceuticals Corporation, 33 Hayden Avenue, Lexington, MA 02421, USA.
authors.forename: Prakash G
authors.initials: PG
authors.lastname: Jagtap
authors.forename: Zhiyu
authors.initials: Z
authors.lastname: Chen
authors.forename: Karsten
authors.initials: K
authors.lastname: Koppetsch
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Piro
authors.forename: Paula
authors.initials: P
authors.lastname: Fronce
authors.forename: Garry J
authors.initials: GJ
authors.lastname: Southan
authors.forename: Karl-Norbert
authors.initials: KN
authors.lastname: Klotz