Polymer-supported syntheses of oligosaccharides: Using dibutylboron triflate to promote glycosylations with glycosyl trichloroacetimidates

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 6985-6988

  Wang, Zhi Guang ^a   Douglas, Stephen P ^a   Krepinsky, Jiri J ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; GLYCOSYLATION; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030599268     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01570-5     Document Type: Article

References (24)

1. 1. Douglas, S.P; Whitfield, D.M; Krepinsky, J.J. J. Am. Chem. Soc. (a) 1991, 113, 5095;
2. (b) 1995, 117, 2116;
3. (c) Krepinsky, J.J.; Douglas, S.P.; Whitfield, D.M. Methods Enzymol. 1994, 242, (Neoglycoconjugates. Part A. Synthesis; Lee, Y. C.; Lee, R. T., Eds.) 280
4. (d) Krepinsky, J.J. 1996 in Modern Methods of Carbohydrate Synthesis (Khan, S. H.; O'Neill, R. A., Eds.), Harwood Academic Publishers;
5. (e) Boons, G.-J. Tetrahedron 1996, 52, 1095; and references therein.
6. 2. (i) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
7. (ii) Toshima, K.; Tatsuta, K. Chem. Revs. 1993, 93, 1503.
8. (iii) Whitfield, D. M.; Douglas, S. P. Glycoconjug. J. 1996, 13, 5.
9. 3. Whitfield, D. M.; Douglas, S. P.; Tang, T. H.; Csizmadia, I.G.; Pang, H. Y. S.; Moolten, F. L.; Krepinsky, J.J. Can. J. Chem. 1994, 72, 2225, and references therein.
10. 4. (a) Douglas, S. P.; Whitfield, D. M.; Krepinsky, J.J. J. Carbohydr. Chem. 1993, 12, 131;
11. (b) Hitchcock, S. A.; Chu-Moyer, M. Y.; Boyer, S. H.; Olson, S. H.; Danishefsky, S. M. J. Am. Chem. Soc. 1995, 117, 5750.
12. 5. Leung, O. T.; Whitfield, D. M.; Douglas, S. P.; Pang, H. Y. S.; Krepinsky, J.J. New J. Chem. 1994, 18, 349, and references therein.
13. 6. Zhang, X. F., Lupescu, N.; Krepinsky, J.J., manuscript in preparation.
14. 3-25%MeOH; sometimes, however, both groups of substances co-eluted).
15. 3).
16. 1H NMR spectrum the same intensity of methyl signals of the acetyl group (at δ=1.94ppm) and the terminal methyl group of methylether polyethylene glycol (at δ=3.38ppm).
17. 3).
18. 3 was added, the mixture was stirred for 10 minutes, and the solids were filtered off through a celite bed. The filtrate was evaporated to dryness and further purified by chromatography on a silica gel column in hexane-ethyl acetate mixtures.
19. 12. Synthetic procedures for these intermediates will be reported elsewhere.
20. 3).
21. 3).
22. 3).
23. 16. (a) Lemieux, R. U. Chem. Canada 1964, 16, 14,
24. (b) Ziegler, T.; Kovác, P.; Glaudemans, C.P.J. Liebigs Ann. Chem. 1990, 613.