An efficient stereospecific method for the synthesis of 8-aza-3-deazaguanine nucleosides from glycosyl azides

Synlett

Volumn , Issue 7, 1999, Pages 1069-1073

  Štimac, Anton ^a,c   Leban, Ivan ^b   Kobe, Jože ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

^c Krka   (Slovenia)

Author keywords

1,2,3 Triazoles; 1,2,3 Triazolo 4,5 c pyridines; Dimroth reaction; Glycosyl azides; Nucleoside analogues

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; AMIDE; AZIDE; DIAMIDE; DRUG ANALOG; NUCLEOSIDE ANALOG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DEHYDRATION; DRUG SYNTHESIS; GLYCOSYLATION; MOLECULAR STABILITY; STEREOSPECIFICITY; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

EID: 0032769745     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2755     Document Type: Article

References (30)

1. Revankar, G. R.; Robins, R. K. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, Vol. 2, 1991, p 161.
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3. Seela, F.; Lampe, S. Helv. Chim. Acta 1991, 74, 1790.
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5. Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323.
6. Meyer, R. B., Jr.; Revankar, G. R.; Cook, P. D.; Ehler, K. W.; Schweizer, M. P.; Robins, R. K. J. Heterocycl. Chem. 1980, 17, 159.
7. Earl, R. A.; Townsend, L. B. Can. J. Chem. 1980, 58, 2550.
8. Štimac, A.; Townsend, L. B.; Kobe, J. Nucleosides, Nucleotides 1991, 10, 727.
9. L'abbe, G. Ind. Chim. Belg. 1971, 36, 3.
10. 3 in DMSO at room temperature for 1 h; 1r, 1u, and 1w, by the liquid-liquid phase transfer catalytic method according to: Tropper, F. D.; Andersson, F. O.; Braun, S.; Roy, R. Synthesis 1992, 618. Details of the preparation of previously unknown substrates as well as those prepared by more stereoselective routes will be given in separate publications.
11. 3 in DMSO at room temperature for 1 h; 1r, 1u, and 1w, by the liquid-liquid phase transfer catalytic method according to: Tropper, F. D.; Andersson, F. O.; Braun, S.; Roy, R. Synthesis 1992, 618. Details of the preparation of previously unknown substrates as well as those prepared by more stereoselective routes will be given in separate publications.
12. 3 in DMSO at room temperature for 1 h; 1r, 1u, and 1w, by the liquid-liquid phase transfer catalytic method according to: Tropper, F. D.; Andersson, F. O.; Braun, S.; Roy, R. Synthesis 1992, 618. Details of the preparation of previously unknown substrates as well as those prepared by more stereoselective routes will be given in separate publications.
13. 3 in DMSO at room temperature for 1 h; 1r, 1u, and 1w, by the liquid-liquid phase transfer catalytic method according to: Tropper, F. D.; Andersson, F. O.; Braun, S.; Roy, R. Synthesis 1992, 618. Details of the preparation of previously unknown substrates as well as those prepared by more stereoselective routes will be given in separate publications.
14. Cottrell, I. F.; Hands, D.; Houghton, P. G.; Humphrey, G. R.; Wright, S. H. B. J. Heterocycl. Chem. 1991, 28, 301.
15. 11 (643.61): C, 61.58; H, 4.54; N, 6.53. Found: C, 61.53; H, 4.54; N, 6.50.
16. The stereochemistry of the Dimroth reaction of glycosyl azides with DOG is in sharp contrast to that observed with cyanoacetamide, which was reported to yield 1,2-trans nucleosides exclusively or predominately from either 1,2-trans or 1,2-cis glycosyl azides: Tolman, R. L.; Smith, C. W.; Robins, R. K. J. Am. Chem. Soc. 1972, 94, 2530; Smith, C. W.; Sidwell, R. W.; Robins, R. K.; Tolman, R. L. J. Med. Chem. 1972, 15, 883; Chretien, F.; Gross, B. Tetrahedron 1982, 38, 103. This difference may be attributed to much more favourable intramolecular triazene N-atom to carbonyl group cyclization in the glycosyl azide-DOG adduct as opposed to the cyclization to cyano group in the glycosyl azide-cyanoacetamide adduct. For this reason, the competitive anomerization process in the former case should be effectively supressed.
17. The stereochemistry of the Dimroth reaction of glycosyl azides with DOG is in sharp contrast to that observed with cyanoacetamide, which was reported to yield 1,2-trans nucleosides exclusively or predominately from either 1,2-trans or 1,2-cis glycosyl azides: Tolman, R. L.; Smith, C. W.; Robins, R. K. J. Am. Chem. Soc. 1972, 94, 2530; Smith, C. W.; Sidwell, R. W.; Robins, R. K.; Tolman, R. L. J. Med. Chem. 1972, 15, 883; Chretien, F.; Gross, B. Tetrahedron 1982, 38, 103. This difference may be attributed to much more favourable intramolecular triazene N-atom to carbonyl group cyclization in the glycosyl azide-DOG adduct as opposed to the cyclization to cyano group in the glycosyl azide-cyanoacetamide adduct. For this reason, the competitive anomerization process in the former case should be effectively supressed.
18. The stereochemistry of the Dimroth reaction of glycosyl azides with DOG is in sharp contrast to that observed with cyanoacetamide, which was reported to yield 1,2-trans nucleosides exclusively or predominately from either 1,2-trans or 1,2-cis glycosyl azides: Tolman, R. L.; Smith, C. W.; Robins, R. K. J. Am. Chem. Soc. 1972, 94, 2530; Smith, C. W.; Sidwell, R. W.; Robins, R. K.; Tolman, R. L. J. Med. Chem. 1972, 15, 883; Chretien, F.; Gross, B. Tetrahedron 1982, 38, 103. This difference may be attributed to much more favourable intramolecular triazene N-atom to carbonyl group cyclization in the glycosyl azide-DOG adduct as opposed to the cyclization to cyano group in the glycosyl azide-cyanoacetamide adduct. For this reason, the competitive anomerization process in the former case should be effectively supressed.
19. All new compounds were characterized by spectroscopic (NMR, IR, and MS) and analytical methods (microanalysis and/or HRMS) including an X-ray analysis of compound 2f. Details will be provided in a full paper.
20. Ammonia, saturated in methanol at 0 °C, was used.
21. Matsuda, A.; Shinozaki, M.; Suzuki, M., Watanabe, K.; Miyasaka, T. Synthesis 1986, 385.
22. Campagna, F.; Carotti, A.; Casini, G. Tetrahedron Lett. 1977, 1813.
23. 4OH at 0 °C, see ref. 7.
24. 4OH at 0 °C, see ref. 7.
25. 4OH at 0 °C, see ref. 7.
26. 5 (283.25): C, 42.41; H, 4.63; N, 24.73. Found: C, 42.15; H, 4.64; N, 24.71.
27. 3: Cook, P. D.; Rousseau, R. J.; Mian, A. M.; Dea, P.; Meyer, R. B., Jr.; Robins, R. K. J. Am. Chem. Soc. 1976, 95, 1492.
28. Hanessian, S.; Liak, T. J.; Vanasse, B. Synthesis 1981, 396.
29. Mansuri, M. M.; Krishnan, B.; Martin, J. C. Tetrahedron Lett. 1991, 32, 1287.
30. Ješelnik, M.; Kobe, J., in preparation.