Lewis acid mediated reductive ring opening of 2-methoxyethylidene acetals: A new approach to 2-methoxyethyl (MOE) ethers of cis-diols

Synlett

Volumn , Issue 16, 2005, Pages 2437-2440

  Hanessian, Stephen ^a   Machaalani, Roger ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Acetal; Antisense; Nucleoside; Reductive opening

Indexed keywords

1,4 ANHYDRO DEXTRO RIBITOL; 2 METHOXYETHYLIDENE ACETAL; 2' O (2 METHOXYETHER) ETHER; 3' O (2 METHOXYETHYL) ETHER; ACETAL DERIVATIVE; ANTISENSE OLIGONUCLEOTIDE; ETHER DERIVATIVE; LEWIS ACID; RIBITOL; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; RING OPENING; SYNTHESIS;

EID: 26844448662     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872686     Document Type: Article

References (30)

1. (a) Beigelman, L.; Harberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047.
2. (b) Ross, B. S.; Springer, R. H.; Tortorici, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641.
3. (c) Chanteloup, L.; Thuong, T. N. Tetrahedron Lett. 1994, 35, 877.
4. (d) Roy, S. K.; Tang, J.-Y. Org. Process Res. Dev. 2000, 4, 170.
5. (e) Von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron 1999, 40, 1873.
6. (f) Beigelmann, L.; Sweedler, D.; Haeberli, P.; Karpeisky, A. US Patent 5,962,275, 1999.
7. (a) Martin, P. Helv. Chim. Acta 1995, 78, 486.
8. (b) Legorburu, U.; Reese, C. B.; Song, Q. Tetrahedron 1999, 55, 5635.
9. (c) Altmann, K.-H.; Bévierre, M.-O.; De Mesmaeker, A.; Moser, H. E. Bioorg. Med. Chem. Lett. 1995, 5, 431.
10. (d) Cook, P. D.; Springer, R. H.; Sprankle, K. G.; Ross, B. S. US Patent 5,861,493, 1999.
11. (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 544.
12. (b) Irgolic, K. J. In Houben-Weyl, Vol. E12b; Klamann, D., Ed.; Thieme: Stuttgart, 1990, 4th ed., 150.
13. Zamecnik, P. C.; Stephenson, M. L. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 280.
14. Kurreck, J. Eur. J. Biochem. 2003, 270, 1628.
15. (a)Antisense Drug Technology; Crooke, S. T., Ed.; Dekker: New York, 2001.
16. (b) Manoharan, M. Biochim. Biophys. Acta 1999, 1489, 117.
17. Martin, P. Helv. Chim. Acta 2003, 86, 204.
18. Chow, S.; Wen, K.; Sanghvi, S. Y.; Theodorakis, E. A. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 583.
19. (a) Sproat, B. S.; Beijer, B.; Groti, M.; Ryder, U.; Morand, K. L.; Lamond, A. I. J. Chem. Soc., Perkin Trans. 1 1994, 419.
20. (b) Hanessian, S.; Lavallée, P. Can. J. Chem. 1975, 53, 2975.
21. For examples of endo- and exo-acetals, see: (a) Venkatesalu, B.; Lin, L. G.; Cherian, X. M.; Czarnik, A. W. Carbohydr. Res. 1987, 170, 124.
22. (b) See also: Grindley, T. B.; Szarek, W. A. Carbohydr. Res. 1972, 25, 187.
23. D +0.78 (c 7.00, MeOH).
24. 3SiH, however, no opening of the acetal was observed under these conditions.
25. Decomposition was observed when MeCN and nitromethane were used as solvent.
26. Hanessian, S.; Machaalani, R. Tetrahedron Lett. 2003, 44, 8321.
27. For example, see: (a) Guindon, Y.; Ogilvie, W. W.; Bordeleau, J.; Li, C. W.; Durkin, K.; Gorys, V.; Juteau, H.; Lemieux, R.; Liotta, D.; Simoneau, B.; Yoakim, C. J. Am. Chem. Soc. 2003, 125, 428.
28. (b) Corcoran, C. R. Tetrahedron Lett. 1990, 31, 2101.
29. (c) Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83.
30. (d) Liptak, A.; Fügedi, P.; Nanasi, P. Carbohydr. Res. 1978, 65, 209.