Synthesis of new acyclonucleosides comprising unexpected regioisomers in the case of purines

Tetrahedron

Volumn 59, Issue 48, 2003, Pages 9635-9639

  Guillarme, Stéphane ^a   Legoupy, Stéphanie ^a   Bourgougnon, Nathalie ^b   Aubertin, Anne Marie ^c   Huet, François ^a  

^a UNIVERSITÉ DU MAINE   (France)

^b Centre de Recherche et d'Enseignement Yves Coppens   (France)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Nucleosides; Purines; Pyrimidines; Regiochemistry

Indexed keywords

ACETIC ACID; ACRYLIC ACID DERIVATIVE; ETHYL 2 HYDROXYMETHYL ACRYLATE; NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; ISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0242289568     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.093     Document Type: Article

References (22)

1. Agrofoglio L.A., Challand S.R. Acyclic, Carbocyclic and L-Nucleosides. 1998;Kluwer Academic, Dordrecht. pp 18-173.
2. (a) Elion G.B., Furman P.A., De Miranda P., Beauchamp L., Schaeffer H.J. Proc. Natl. Acad. Sci. USA. 74:1977;5716-5720
3. (a) Elion G.B., Furman P.A., De Miranda P., Beauchamp L., Schaeffer H.J. Proc. Natl. Acad. Sci. USA. 74:1977;5716-5720 (b) Schaeffer H.J., Beauchamp L., De Miranda P., Elion G.B., Bauer D.J., Collins P. Nature (London). 272:1978;583.
4. (a) Martin J.C., Dvorak C.A., Smee D.F., Matthews T.R., Verheyden J.P.H. J. Med. Chem. 26:1983;759-761
5. (a) Martin J.C., Dvorak C.A., Smee D.F., Matthews T.R., Verheyden J.P.H. J. Med. Chem. 26:1983;759-761 (b) Meier C., Habel C., Haller-Meier F., Lomp A., Herderich M., Klöcking R., Meerbach A., Wultzler P. Antiviral Chem. Chemother. 9:1998;389-402.
6. (a) Guillarme S., Legoupy S., Aubertin A.-M., Olicard C., Bourgougnon N., Huet F. Tetrahedron. 59:2003;2177-2184
7. (a) Guillarme S., Legoupy S., Aubertin A.-M., Olicard C., Bourgougnon N., Huet F. Tetrahedron. 59:2003;2177-2184 (b) Hubert C., Alexandre C., Aubertin A.-M., Huet F. Tetrahedron. 59:2003;3127-3130.
8. (a) Balzarini J., Kang G.J., Dalal M., Herdewijn P., De Clercq E., Broder S., Johns D.G. Mol. Pharmacol. 32:1987;162-167
9. (a) Balzarini J., Kang G.J., Dalal M., Herdewijn P., De Clercq E., Broder S., Johns D.G. Mol. Pharmacol. 32:1987;162-167 (b) Barrish J.C., Zahler R. Antiviral agents. Ann. Rep. Med. Chem. 28:1993;131-140.
10. Byun H.S., Reddy K.C., Bittman R. Tetrahedron Lett. 35:1994;1371-1374.
11. Tendler S.J.B., Threagill M.D., Tisdale M.J. J. Chem. Soc., Perkin Trans. 1. 1987;2617-2623. and references therein.
12. Gras J.-L., Kong Win Chang Y.-Y., Guerin A. Synthesis. 1985;74-75.
13. Beauchamp L.M., Tuttle J.V., Rodriguez M.E., Sznaidman M.L. J. Med. Chem. 39:1996;949-956.
14. (a) Vorbrüggen H., Krolikiewicz K., Bennua B. Chem. Ber. 114:1981;1234-1255
15. (b) Vorbrüggen H., Holfe G. Chem. Ber. 114:1981;1256-1268
16. (a) Vorbrüggen H., Krolikiewicz K., Bennua B. Chem. Ber. 114:1981;1234-1255 (b) Vorbrüggen H., Holfe G. Chem. Ber. 114:1981;1256-1268 (c) Vorbrüggen H., Bennua B. Chem. Ber. 114:1981;1279-1286.
17. Dudycz L., Wright G.E. Nucleosides Nucleotides. 3:1984;33-44.
18. Robins M.J., Zou R., Guo Z., Wruk S.F. J. Org. Chem. 61:1996;9207-9212.
19. Cheung A.W.-H., Sidduri A., Garofulo L.M., Goodnow R.A. Jr. Tetrahedron Lett. 41:2000;3303-3307.
20. Perrin D.D., Armarego W.L.F. Purification of Laboratory Chemicals. 3rd ed. 1988;Pergamon, Berlin.
21. Weigand S., Brueckner R. Synthesis. 1996;475-482.
22. Robins M.J., Zou R., Guo Z., Wnuk S.F. J. Org. Chem. 62:1996;9207-9212. and references therein.