An improved approach to the synthesis of adenosine-5′-N-ethyluronamides of interest as adenosine receptor agonists

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1567-1570

  Ha, Seung B ^a   Nair, Vasu ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE 5' (N ETHYLCARBOXAMIDE) DERIVATIVE; ADENOSINE DERIVATIVE; ADENOSINE RECEPTOR STIMULATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029872804     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00092-5     Document Type: Article

References (18)

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11. 6) δ 1.35 (s, 3H), 1.52 (s, 3H), 4.67 (s, 1H), 5.50 (m, 2H), 6.32 (s, 1H), 7.26 (br s, 2H), 8.08 (s, 1H), 8.26 (s, 1H).
12. 6) δ 0.92 (t, 3H), 1.35 (s, 3H), 1.52 (s, 3H), 3.77 (m, 2H), 4.86 (s, 1H), 5.51 (m, 2H), 6.43 (s, 1H), 8.24 (br s, 2H), 8.30 (s, 1H), 8.46 (s, 1H).
13. Nair, V.; Richardson, S. G. J. Org. Chem. 1980, 45, 3969-3974.
14. Nair, V.; Richardson, S. G. Synthesis 1982, 670-672.
15. Nair, V.; Fasbender, A. J. Tetrahedron 1993, 49, 2169-2184.
16. 6) δ 1.03 (t, 3H), 1.43 (s, 3H), 1.62 (s, 3H), 3.87 (m, 2H), 4.85 (s, 1H), 5.56 (m, 2H), 6.29 (s, 1H), 8.32 (s, 1H), 8.67 (s, 1H).
17. 2. The reaction mixture was stirred at room temperature for 12 h. The solvent was removed under reduced pressure and the product was purified by flash column chromatography on silica gel.
18. 4: C, 63.93; H, 5.78; N, 17.20. Found: C, 63.56; H, 5.54; N, 16.74.