[N,1-15N2]-2′-deoxyadenosines

Organic Letters

Volumn 7, Issue 12, 2005, Pages 2477-2479

  Terrazas, Montserrat ^a   Ariza, Xavier ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMMONIUM DERIVATIVE; BENZENE DERIVATIVE; CHLORINE DERIVATIVE; CYANIDE; DEOXYADENOSINE DERIVATIVE; INOSINE DERIVATIVE; NITROGEN DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS;

CATALYSIS; CYCLIZATION; DEOXYADENOSINES; INOSINE; MOLECULAR STRUCTURE; NITROGEN ISOTOPES; PALLADIUM;

EID: 20544439355     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050788w     Document Type: Article

References (31)

1. For reviews, see: (a) Kawashima, E.; Kamaike, K. Mini-Rev. Org. Chem. 2004, 1, 309.
2. (b) Lagoja, I. M.; Herdewijn, P. Synthesis 2002, 301.
3. (c) Milecki, J. J. Labelled Compd. Radiopharm. 2002, 45, 307.
4. Also see: (d) Shallop, A. J.; Gaffney, B. L.; Jones, R. A. J. Org. Chem. 2003, 68, 8657 and references therein.
5. (e) Abad, J.-L.; Gaffney, B. L.; Jones, R. A. J. Org. Chem. 1999, 64, 6575 and references therein.
6. For recent representative examples, see: (a) Wenter, P.; Pitsch, S. Helv. Chim. Acta 2003, 86, 3955.
7. (b) Gorchs, O.; Hernández, M.; Garriga, L.; Pedroso, E.; Grandas, A.; J. Farràs, J. Org. Lett. 2002, 4, 1827.
8. (c) Dunger, A.; Limbach, H.-H.; Weisz, K. J. Am. Chem. Soc. 2000, 122, 10109.
9. (d) Matsuo, H.; Moriguchi, T.; Takagi, T.; Kusakabe, T.; Buratowski, S.; Sekine, M.; Kyogoku, Y.; Wagner, G. J. Am. Chem. Soc. 2000, 122, 2417.
10. (a) Ariza, X.; Bou, V.; Vilarrasa, J. J. Am. Chem. Soc. 1995, 117, 3665.
11. (b) Terrazas, M.; Ariza, X.; Farràs, J.; Guisado-Yang, J. M.; Vilarrasa, J. J. Org. Chem. 2004, 69, 5473 and references therein.
12. For the use of 4-nitrophenyl and 2,4-dinitrophenyl derivatives in the deoxyinosine series, see: (a) De Napoli, L.; Messere, A.; Montesarchio, D.; Piccialli, G. J. Org. Chem. 1995, 60, 2251.
13. (b) Catalanotti, B.; De Napoli, L.; Galeone, A.; Mayol, L.; Oliviero, G.; Piccialli, G.; Varra, M. Eur. J. Org. Chem. 1999, 2235 and references therein.
14. 3/PhCOCl. For a review, see: Romea, P.; Aragonès, M.; Garcia, J.; Vilarrasa, J. J. Org. Chem. 1991, 56, 7038. That the sensitivity of deoxypurine nucleosides regarding the anomeric bond cleavage is larger than that of the other natural nucleosides is a well-known fact.
15. For reviews of alternative uses of the Ns group, see: (a) Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353.
16. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1999.
17. NsCl (oNsCl) is much cheaper than pNsCl. Moreover, the Ns group is cleaved more selectively when used as a protecting group, see: (a) Wuts, P. G. M.; Northuis, J. M. Tetrahedron Lett. 1998, 39, 3889. We disclose here another advantage of Ns vs pNs (lower percentages of desulfonylation), as the o-nitro partially blocks the attack at the S of the sulfonyl group.
18. 2) = 18.3 Hz), 160.5, 170.3, 170.5.
19. 3CN, without DBU, the highest yield was 63%.
20. 3CN turned out to be much slower, and byproducts coming from the attack at S were produced in higher percentages.
21. (a) Véliz, E. A.; Beal, P. A. J. Org. Chem. 2001, 66, 8592.
22. (b) Véliz, E. A.; Beal, P. A. Tetrahedron Lett. 2000, 41, 1695.
23. 3CN and slowly warmed to 70 °C; however, this afforded the corresponding 6-(dimethylamino)purine nucleoside as the major compound (not the desired bromo derivative).
24. (a) Liu, J.; Janeba, Z.; Robins, M. J. Org. Lett. 2004, 6, 2917.
25. (b) Janeba, Z.; Francom, P.; Robins, M. J. J. Org. Chem. 2003, 68, 989.
26. 3N (ref 3a).
27. Purchased from Fluka. For classical works on the use of dppf, see: (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158 and references therein.
28. For Pd-catalyzed couplings of amides, see: (b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653 and references therein.
29. For Buchwald-Hartwig aminations with aryl and heteroaryl chlorides, see: (c) Urgaonkar, S.; Verkade, J. G. J. Org. Chem. 2004, 69, 9135 and references therein.
30. (d) Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371.
31. +) 358.1299.