Synthesis of novel C-nucleosides with potential applications in combinatorial and parallel synthesis

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 575-578

  Adlington, Robert M ^a   Baldwin, Jack E ^a   Pritchard, Gareth J ^a   Spencer, Keith C ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYRIBOSE; ACETYLENE DERIVATIVE; AMIDINE; C NUCLEOSIDE; KETONE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034700826     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02078-X     Document Type: Article

References (15)

1. Adlington, R. M.; Baldwin, J. E.; Pritchard, G. J.; Catterick, D. J. Chem. Soc., Perkin 1 1999, 855.
2. Adlington, R. M.; Baldwin, J. E.; Pritchard, G. J.; Catterick, D. J. Chem. Soc., Chem. Commun. 1997, 1757.
3. (a) Barton, D. H. R.; Ramesh, M. J. Am. Chem. Soc. 1990, 112, 891.
4. (b) Kang, S. O.; Lee, S. B. J. Chem. Soc., Chem. Commun. 1995, 1017.
5. For reviews, see: Perigaud, C.; Gosselin, G.; Imbach, J.-L. Nucleosides Nucleotides 1992, 11, 903.
6. Bernardo, S. D.; Weigele, M. J. Org. Chem. 1976, 41, 287.
7. Chaudhuri, N. C.; Ren, R. X.-F.; Kool, E. T. Synlett 1997, 341.
8. Fox has described related methodology as a route to pyrimidin-4-ones, see: Tam, S. Y.-K.; Heras, F. G. D. L.; Klein, R. S.; Fox, J. J. Tetrahedron Lett. 1975, 38, 3271.
9. Rolland, V.; Kotera, M.; Lhomme, J. Synth Commun. 1997, 27, 3505.
10. Brimacombe, J. S.; Fletcher, H. G. Methods Carbohydr. Chem. 1972, 6, 373.
11. Jung, M. E.; Trifunovich, I.; Gardiner, J.; Clevenger, G. L. J. Chem. Soc., Chem. Commun. 1990, 84.
12. Confirmed by NOE experiments on both epimers.The anomeric configuration of all anomers were confirmed by NOE experiments based on the known configuration of substituents at C3 and C4.
13. Cupps, T. L.; Boutin, R. H.; Rapoport, H. J. Org. Chem. 1985, 50, 3972.
14. A more direct route to separate α and β anomers using only benzoyl-protecting groups was unsuccessful due to the failure to form an acetylenic ketone from the benzoyl analogue of 7. Other routes using Lewis acid catalysed addition of trimethylsilyl acetylenes, and Stille cross-coupling reactions on stannyl acetylenes, all failed.
15. Yields of C-nucleosides, 13 and 14(c-e) were calculated from the starting benzyl protected C-nucleosides, 9(c-e). Deprotected C-nucleosides 13 and 14(c-e) were purified by column chromatography on silica gel using an appropriate solvent system.