Extended alkenyl glycosides by ruthenium-catalyzed cross-metathesis reaction and application toward novel C-linked pseudodisaccharides

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5408-5412

  Roy, René ^a   Dominique, Romyr ^a   Das, Sanjoy K ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; BENZYLIDENE DERIVATIVE; DISACCHARIDE; GALACTOSIDE; GLYCOSIDE; PYRANOSIDE; RUTHENIUM;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS; TRANS ISOMER;

EID: 0033597743     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9900984     Document Type: Article

References (40)

1. (a) Quignard, F.; Lecoute, M.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1985, 1816.
2. (b) Couturier, J.-L.; Paillet, C.; Lecoute, M.; Basset, J.-M.; Weiss, K. Angew. Chem., Int. Ed. Eng. 1992, 31, 628.
3. (c) Couturier, J.-L.; Tanaka, K.; Lecoute, M.; Basset, J.-M.; Ollivier, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 112.
4. (a) Bagan, G. C.; Khosravi, E.; Schrock, R. R.; Feast, W. J.; Gibson, V. C.; O'Regan, M. B.; Thomas, J. K.; Davis, W. M. J. Am. Chem. Soc. 1990, 112, 8378.
5. (b) Schrock, R. R.; Murdzek, G. C.; Dimare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
6. Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998.
7. Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162.
8. (a) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117.
9. (b) Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441.
10. (a) Descotes, G.; Ramja, J.; Basset. J. M.; Pagano, S. Tetrahedron Lett. 1994, 35, 7379.
11. (b) Ramja, J.; Descotes, G.; Basset, J. M.; Mutch, A. J. Carbohydr. Chem. 1996, 15, 125.
12. (a) Schawab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
13. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
14. For recent reviews, see (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Schwab, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1, 1998, 371.
15. For recent reviews, see (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Schwab, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1, 1998, 371.
16. For recent reviews, see (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Schwab, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1, 1998, 371.
17. (d) Biagini, S. C. G.; Gibson, S. E.; Keen, S. P. J. Chem. Soc., Perkin Trans. 1, 1998, 2487.
18. Dominique, R.; Das, S. K.; Roy, R. J. Chem. Soc., Chem. Commun. 1998, 2437.
19. For reviews, see (a) Roy, R. In Carbohydrate Chemistry; Boons, G. J., Ed.; Chapman & Hall: London, UK, 1998; p 243. (b) Roy, R. In Topics in Current Chemistry Thiem, J., Driguez, H., Eds.; Springer: Heidelberg, 1997; Vol. 187, p 241.
20. For reviews, see (a) Roy, R. In Carbohydrate Chemistry; Boons, G. J., Ed.; Chapman & Hall: London, UK, 1998; p 243. (b) Roy, R. In Topics in Current Chemistry Thiem, J., Driguez, H., Eds.; Springer: Heidelberg, 1997; Vol. 187, p 241.
21. Karlsson, K. A. Cur. Opin. Struct. Biol. 1995, 5, 622.
22. (a) O'Leary, D. J.; Miller, S. J.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 1689.
23. (b) Nishioka, T.; Iwabuchi, Y.; Hatakeyama, S. Tetrahedron Lett. 1998, 39, 5597.
24. (c) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1896, 37, 547.
25. (d) Meng, D.; Bertinato, P.; Balog, A.; Su, D. S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073.
26. (e) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356.
27. (f) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268.
28. (a) Gibson, S. E.; Gibson, U. C.; Keen, S. P. Chem. Commun. 1997, 1107.
29. (b) Brummer, O.; Buckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441.
30. (c) Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun. 1997, 823.
31. (d) O'Leary, D. L.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427.
32. Winnik, F. M.; Carver, J. P.; Krepinski, J. J. J. Org. Chem. 1982, 47, 2701.
33. (a) Sarkar, T. K. Synthesis 1990, 969.
34. (b) Chan, T. H.; Wang, D. Chem. Rev. 1992, 92, 995.
35. (a) Diver, S. T.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 5106.
36. (b) Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy. High Resolution Methods and Applications in Organic Chemistry and Biochemistry; VCH: New York, 1987; p 192.
37. For a review, see; Du, Y.; Linhardt, R. J.; Vlahou, I. R. Tetrahedron 1998, 54, 9913.
38. Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479.
39. Brimacombe, J. S.; Kabir, A. K. M. S. Carbohydr. Res. 1986, 150, 35.
40. Fraser-Reid, B.; Udolong, U. E.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett 1992, 927.