Photochemistry on Soluble Polymer Supports: Synthesis of Nucleosides

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4415-4417

  Zhong, Jian Hua ^a   Fishman, Alex ^a   Lee Ruff, Edward ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; KETONE; MACROGOL DERIVATIVE; NUCLEOSIDE; POLYMER; RIBONUCLEOSIDE;

ARTICLE; CHEMISTRY; PHOTOCHEMISTRY; SYNTHESIS;

CYCLOBUTANES; KETONES; NUCLEOSIDES; PHOTOCHEMISTRY; POLYETHYLENE GLYCOLS; POLYMERS; RIBONUCLEOSIDES;

EID: 0037069704     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026881r     Document Type: Article

References (19)

1. DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
2. (a) Lee-Ruff, E.; Jandrisits, L.; Hayes, I. E. E. Can. J Chem. 1989, 67, 2057.
3. (b) Lee-Ruff, E.; Jiang, J.-L.; Wan, W.-Q. Tetrahedron Lett. 1993, 34, 261.
4. (c) Lee-Ruff, E.; Wan, W.-Q. J. Org. Chem. 1994, 59, 2114.
5. (d) Lee-Ruff, E.; Xi, F.-D.; Qie, J.-H. J. Org. Chem. 1996, 61, 1547.
6. (e) Lee-Ruff, E.; Ostrowski, M.; Ladha, A.; Stynes, D. V.; Vernik, I.; Jiang, J.-L.; Wan, W.-Q.; Ding, S. F.; Joshi, S. J. Med. Chem. 1996, 39, 5276.
7. (f) Lee-Ruff, E.; Margau, R. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 185-196.
8. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
9. Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
10. Fishman, A.; Farrah, M. E.; Zhong, J.-H.; Lee-Ruff, E. Manuscript in preparation.
11. Vorbrüggen, H.; Ruh-Pohlenz, C. Org. React. 2000, 55, 1.
12. Lee-Ruff, E. In New Synthetic Pathways from Cyclobutanones in Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London, 1991; Vol. 1, p 167.
13. 1H NMR analysis.
14. Bamford, M. J.; Humber, D. C.; Storer, R. Tetrahedron Lett. 1991, 32, 271.
15. 4. After the solution was concentrated, cold anhydrous ether was added whereupon the polymer precipitated out and was filtered off. The filtrated was evaporated, and the residue was chromatographed on preparative TLC plates (repeated elution with 1:1 hexane/ethyl acetate) to give 0.088 g (0.24 mmol) of 9α and 0.171 g (0.48 mmol) of 9β.
16. Séquin, E.; Tamm, C. Helv. Chim. Acta 1972, 55, 1196.
17. 1H NMR and UV spectra to those previously reported; cf.: Sells, T. B.; Nair, V. Tetrahedron 1994, 50, 117.
18. Sunder, A.; Hanselmann, R.; Frey, H.; Mülhaupt, R. Macromolecules 1999, 32, 4240.
19. Lubineau, A.; Malleron, A.; Le Narvor, C. Tetrahedron Lett. 2000, 41, 8887.