Synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde: application to the synthesis of potent adenosine A2A and A3 receptor agonist

Tetrahedron Letters

Volumn 50, Issue 22, 2009, Pages 2693-2696

  Jagtap, Prakash G ^a   Chen, Zhiyu ^a   Koppetsch, Karsten ^a   Piro, Elizabeth ^a   Fronce, Paula ^a   Southan, Garry J ^a   Klotz, Karl Norbert ^b  

^a INOTEK CORPORATION   (United States)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETOXYMETHYL 3,4 DIHYDRO 2H PYRAN; 3,4 DIHYDRO 2H PYRAN 2 CARBOXALDEHYDE; 3,4 DIHYDRO 2H PYRANYL; ADENOSINE 5' (N ETHYLCARBOXAMIDE); ADENOSINE A2A RECEPTOR; ADENOSINE A2A RECEPTOR AGONIST; ADENOSINE A3 RECEPTOR; ADENOSINE A3 RECEPTOR AGONIST; ALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; ENZYME KINETICS; ENZYME MECHANISM; RECEPTOR AFFINITY;

EID: 64249105654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.148     Document Type: Article

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38. 3) δ 1.56-2.07 (m, 4H), 4.29-4.32 (dd, J = 5.4 and 7.5 Hz, 1H), 4.77-4.79 (m, 1H), 6.49 (d, J = 6.3 Hz, 1H), 9.71 (s, 1H). Compound (R)-7 was found to be unstable if exposed to heat and light. It was stored in a refrigerator using the dark vials.
39. 6) δ 1.04 (t, J = 6.6 Hz, 3H), 1.89-2.08 (m, 4H), 3.15-3.20 (m, 3H), 4.22-4.24 (m, 1H), 4.36 (d, J = 3.6 Hz, 1H), 4.55-4.61 (m, 2H), 4.80 (d, J = 5.4 Hz, 1H), 5.69 (s, 2H), 5.91 (d, J = 6.3 Hz, 1H), 6.49 (d, J = 6.3 Hz, 1H), 7.56 (d, J = 5.4 Hz, 1H), 8.25 (t, J = 5.1 Hz, 1H), 8.59 (s, 1H).