Synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde: application to the synthesis of potent adenosine A(2A) and A(3) receptor agonist.
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).
Jagtap
Prakash G
PG
Inotek Pharmaceuticals Corporation, 33 Hayden Avenue, Lexington, MA 02421, USA.
Chen
Zhiyu
Z
Koppetsch
Karsten
K
Piro
Elizabeth
E
Fronce
Paula
P
Southan
Garry J
GJ
Klotz
Karl-Norbert
KN