A General Synthesis of N-Glycosides. I. Synthesis of Pyrimidine Nucleosides

Journal of Organic Chemistry

Volumn 39, Issue 25, 1974, Pages 3654-3660

  Niedballa, U ^a   Vorbruggen H ^a  

^a Department Allgemeine Synthetische Chemie ^*  (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

TRIAZINE DERIVATIVE;

3' METHYLCOCAINE; DIHYDROPYRIMIDINE; DIHYDROPYRIMIDINE DERIVATIVE; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TETRAHYDROPYRIMIDINE DERIVATIVE; THEORETICAL STUDY; THIN LAYER CHROMATOGRAPHY; TRIAZINONE DERIVATIVE;

AZAURIDINE; CHEMISTRY; GLYCOSIDES; METHODS; PYRIMIDINE NUCLEOSIDES; SILICON;

EID: 0016351762     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00939a008     Document Type: Article

References (71)

1. U. Niedballa and H. Vorbrüggen, Angew. Chem., Int. Ed. Engl., 9, 461 (1970)
2. Part II: Synthesis of 6-Methyluridines, J. Org. Chem., 39, 3660 (1974)
3. Part III: Synthesis of Pyrimidine Disaccharide Nucleosides, J. Org. Chem., 39, 3664 (1974)
4. Part IV: Synthesis of Nucleosides of Hydroxy and Mercapto N-Heterocycles. J. Org. Chem., 39, 3668 (1974)
5. Part V: Synthesis of 5-Azacytidines, J. Org. Chem., 39, 3668 (1974)
6. W. W. Zorbach, Synthesis, 329 (1970)
7. K. A. Watanabe and J. J. Fox, J. Heterocycl. Chem., 6, 109 (1969)
8. J. Pliml and M. Prystaš, Advan. Heterocycl. Chem., 8, 115 (1967)
9. L. Birkhofer, A. Ritter, and H. P. Kühlthau, Angew. Chem., 75, 209 (1963)
10. L. Birkhofer, A. Bitter and H. P. Kühlthau, Chem. Ber., 97, 934 (1964)
11. T. Nishimura, B. Shimizu, and I. Iwai, Chem. Pharm. Bull. (Tokyo), 11, 1470 (1963)
12. T. Nishimura and I. Iwai, Chem. Pharm. Bull. (Tokyo), 12, 357 (1964)
13. E. Wittenburg, Z. Chem., 4, 303 (1964)
14. E. Wittenburg, Chem. Ber., 101, 1095 (1968)
15. H. Vorbrüggen, P. Strehlke, and G. Schulz, Angew. Chem., Int. Ed. Engl., 8, 976 (1969)
16. H. Vorbrüggen and P. Strehlke, Chem. Ber., 106, 3039 (1973)
17. M. Prystaš and F. Šorm, Collect. Czech. Chem. Commun., 27, 1578 (1962)
18. A. R. Restivo and F. A. Donzila, J. Org. Chem., 27, 2281 (1962)
19. Y. Mizuno, M. Ikehara, and K. A. Watanabe, Chem. Pharm. Bull. (Tokyo), 11, 293 (1963)
20. C. Cristescu, Rev. Roumaine Chim., 12, 365 (1968)
21. E. Wittenburg, presented at the XXI IUPAC Congress, Prague, Sept. 4
22. F. v. Arlt, Monatsh. Chem., 22, 144 (1901)
23. L. J. Haynes and F. H. Newth, Advan. Carbohyd. Chem., 10, 207 (1955)
24. B. R. Baker, R. E. Schaub, and H. M. Kissman, J. Amer. Chem. Soc., 77, 5911 (1955)
25. Y. Furakawa and M. Honjo, Chem. Pharm. Bull. (Tokyo), 16, 1076 (1968)
26. H. Vorbrüggen and U. Niedballa, Angew. Chem., Int. Ed. Engl., 10, 657 (1971)
27. H. Vorbrüggen, K. Krolíkíewicz, and U. Niedballa, submitted for publication In Justus Liebigs Ann. Chem.
28. M. Muraoka, A. Takada, and T. Ueda, Chem. Pharm. Bull. (Tokyo), 18, 261 (1970)
29. E. H. Hamamura, K. Sato, and J. G. Moffatt, J. Med. Chem., 15, 1061 (1972)
30. T. Ueda and H. Nishino, J. Amer. Chem. Soc., 90, 1678 (1968)
31. S. Nishimura in “Progress in Nucleic Acid Research and Molecular Biology,” Vol. 12, J. N. Davidson and W. Cohn, Ed., Academic Press, New York-London, 1972 p 49
32. M. Prystaš and F. Sorm, Collect. Czech. Chem. Commun., 29, 2956 (1964)
33. R. D. Guthrie and S. C. Smith, Chem. Ind. (London), 547 (1968)
34. P. Roy-Durman “Analogues of Nucleic Acid Compounds,” Springer Verlag, Berlin-Heidelberg-New York, 1970, pp 42-45
35. R. J. Ferrler, Fortschr. Chem. Forsoh., Topics Curr. Chem., 14, 389 (1970)
36. R. E. Deriaz, W. G. Overand, M. Stacey, and L. F. Wiggins, J. Chem. Soc. (London), 2836 (1949)
37. M. Hoffer, Chem. Ber., 93, 2777 (1960)
38. M. P. Kotick, C. Szantay, and T.H. J. Bardos, J. Org. Chem., 34, 3806 (1969)
39. M. Swɨerkowski and D. Shugar, J. Med. Chem., 12, 533 (1969)
40. J. Farkas, J. Beránek, and F. Sorm, Collect. Czech. Chem. Commun., 31, 4002 (1966)
41. J. Beránek and F. Sorm, Czech. Chem. Commun., 33, 913 (1968)
42. M. J. Robins and R. K. Robins, J. Amer. Chem. Soc., 87, 4934 (1965)
43. R. Baker and H. G. Fletcher, Jr., J. Org. Chem., 26, 4605 (1961)
44. B. R. Baker, J. P. Joseph, R. E. Schaub, and J. H. Williams, J. Org. Chem., 19, 1786 (1954)
45. J. J. Fox and I. Wempen, Advan. Carbohyd. Chem., 14, 283 (1959)
46. H. G. Fletcher, Trans. N.Y. Acad. Sci., 30, 649 (1968)
47. H. Paulsen, Advan. Carbohyd. Chem. Biochem., 26, 127 (1971)
48. H. Paulsen, Chem. Abstr., 71, 30436e (1969)
49. S. Hiller, M. Lidaks, R. A. Zhuk, A. Berzina, K. Pecs, I. N. Getsova, and E. J. Bruk, Khim. Geterotsikl. Soedin., 375 (1969)
50. R. Brossmer and V. Eschenfelder, Justus Liebigs Ann. Chem., 762, 160 (1972)
51. R. A. Earl and L. B. Townsend, J. HeterocycL Chem., 9, 1141 (1972)
52. J. J. Ritter and P. P. Minien, J. Amer. Chem. Soc., 70, 4045 (1948)
53. L. I. Krimen and D. J. Cota, Org. React., 17, 213 (1969)
54. D. Heller and G. Wagner, Pharmazie, 26, 290 (1971)
55. T. Rogers, R. S. Shadbolt, and T. L. V. Ulbricht, J. Chem. Soc. C, 207 (1969)
56. H. Ohrui, H. Kuzuhara, and S. Emoto, Tetrahedron Lett., 4267 (1971)
57. K. A. Watanabe, I. M. Wempen, and J. J. Fox, Carbohyd. Res., 21, 148 (1972)
58. D. H. Warnock, K. A. Watanabe, and J. J. Fox, Carbohyd. Res., 18, 127 (1971)
59. G. Kowollik, G. Demirow, M. Schütt, and P. Langen, Z. Chem., 12, 106 (1972)
60. D. S. Wise and L. B. Townsend, J. Heterocycl. Chem., 9, 1461 (1972)
61. A. H. Haynes, Tetrahedron, 29, 2807 (1973).
62. G. H. Ransford, R. P. Glinski and M. B. Sporn, Abstracts of Papers of the 165th National Meeting of the American Chemical Society, Dallas, Texas, April 1973, CARB 17
63. G. Quinkert, B. Wegemund, F. Homburg, and G. Cimbollek, Chem. Ber., 97, 958 (1964)
64. E. F. Recondo and H. Rinderknecht, Helv. Chim. Acta, 42, 1171 (1959)
65. P. A. Levene and R. St. Tipson, J. Biol. Chem., 92, 109 (1931)
66. H. Zinner, Chem. Ber., 83, 153 (1950)
67. S. Tejima and H. G. Fletcher, Jr., J. Org. Chem., 28, 2999 (1963)
68. C. P. J. Glaudemans and H. G. Fletcher, Jr., J. Org. Chem., 28, 3004 (1963)
69. J. Gut, Collect. Czech. Chem. Commun., 23, 1588 (1958)
70. J. Beranek and J. Šorm, German Patent 1445602 (1969)
71. T. E. Johnson and E. F. Schröder, J. Amer. Chem. Soc., 53, 1989 (1931)