Acetamidoglycosylation with glycal donors: A one-pot glycosidic coupling with direct installation of the natural C(2)-N-acetylamino functionality

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 204-207

  Di Bussolo, Valeria ^b   Liu, Jing ^a   Huffman, Larry G ^a   Gin, David Y ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

Carbohydrates; Glycals; Glycosylations; Nitrogen transfer

Indexed keywords

CARBOHYDRATE; GLYCOSIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; FOURIER TRANSFORMATION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034598487     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39:1<204::AID-ANIE204>3.0.CO;2-Z     Document Type: Article

References (37)

1. a) R. A. Dwek, Chem. Rev. 1996, 96, 683-720;
2. b) Synthetic Oligosaccharides. Indispensable Probes for the Life Sciences (Ed.: P. Kovac), ACS Symposium Series 560, American Chemical Society, Washington DC, 1994.
3. J. Banoub, P. Boullanger, D. Lafont, Chem. Rev. 1992, 92, 1167-1195.
4. R. U. Lemieux, T. L. Nagabhushan, Can. J. Chem. 1968, 46, 401-403.
5. R. U. Lemieux, R. M. Ratcliffe, Can. J. Chem. 1979, 57, 1244-1251.
6. a) S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. 1996, 108, 1482-1522; Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419;
7. a) S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. 1996, 108, 1482-1522; Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419;
8. b) D. A. Griffith, S. J. Danishefsky, J. Am. Chem. Soc. 1991, 113, 5863-5864;
9. c) D. A. Griffith, S. J. Danishefsky, J. Am. Chem. Soc. 1990, 112, 5811-5819.
10. D. Lafont, G. Descotes, Carbohydr. Res. 1988, 175, 35-48.
11. a) Y. Leblanc, B. J. Fitzsimmons, J. P. Springer, J. Rokach, J. Am. Chem. Soc. 1989, 111, 2995-3000;
12. b) B. J. Fitzsimmons, Y. Leblanc, N. Chan, J. Rokach, J. Am. Chem. Soc. 1988, 110, 5229-5231;
13. c) B. J. Fitzsimmons, Y. Leblanc, J. Rokach. J. Am. Chem. Soc. 1987, 109, 285-286.
14. J. Du Bois, C. S. Tomooka, J. Hong, E. M. Carreira, J. Am. Chem. Soc. 1997, 119, 3179-3180.
15. For additional methods, see a) E. Kozlowska-Gramz, G. Descotes, Can. J. Chem. 1982, 60, 558-563;
16. b) H. Driguez, J.-P. Vermes, J. Lessard, Can. J. Chem. 1978, 56, 119-130;
17. c) J. Das, R. R. Schmidt, Eur. J. Org. Chem. 1998, 1609-1613.
18. Readily prepared by the treatment of commercially available thianthrene with one equivalent of m-chloroperoxybenzoic acid at 0 C.
19. For reports on the activation of the sulfoxide functionality with triflic anhydride, see a) V. G. Nenajdenko, P. V. Vertelezkij, I. D. Gridnev, N. E. Shevchenko, E. S. Balenkova, Tetrahedron 1997, 53, 8173-8180;
20. b) J. B. Hendrickson, S. M. Schwartzman, Tetrahedron Lett. 1975, 273-276;
21. c) M. D. Coburn, H. H. Hayden, Synthesis 1986, 490-492;
22. d) E. J. Corey, D. Y. Gin, R. S. Kania, J. Am. Chem. Soc. 1996, 118, 9202-9203;
23. e) B. A. Garcia, J. L. Poole, D. Y. Gin, J. Am. Chem. Soc. 1997, 119, 7597-7596;
24. f) V. Di Bussolo, Y.-J. Kim, D. Y. Gin, J. Am. Chem. Soc. 1998, 120, 13515-13516;
25. g) D. Kahne, S. Walker, Y. Cheng, D. Van Engen, J. Am. Chem. Soc. 1989, 111, 6881-6882;
26. h) L. Yan, D. Kahne, J. Am. Chem. Soc. 1996, 118, 9239-9248;
27. i) D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198-1199.
28. For an example of glycal activation with sulfonium reagents, see S. Ramesh, N. Kaila, G. Grewal, R. W. Franck, J. Org. Chem. 1990, 55, 5-7.
29. The use of other acid scavengers such as triethylamine, diisopropylethylamine, and N-methylmorpholine led to poor yields of the glycoside products.
30. Additionally, the N-TMS protective group significantly increases the solubility of the amide reagent at low temperature.
31. The analytical data for the product of the acetamidoglycosylation of benzyl alcohol with 1 in entry 1 was found to be identical in all respects to that previously reported. See: A. Mbongo, C. Fréchou, D. Beaupère, R. Uzan, G. Demailly, Carbohydr. Res. 1993, 246, 361-370.
32. H. Hashimoto, K. Asano, F. Fujii, J. Yoshimura, Carbohydr. Res. 1982, 104, 87-104.
33. The glucal donor in entry 4 was prepared from the 3,4-di-O-benzylation (NaH, BnBr) of 6-O-triisopropylsilyl-D-glucal. For a related procedure, see D. M. Gordon, S. J. Danishefsky, J. Am. Chem. Soc. 1992, 114, 659-663.
34. The glucal donor in entries 8-10 was synthesized by the 6-O-allylation (NaH, Allyl-Br) of 3,4-di-O-benzyl-D-glucal. For a preparation of 3,4-di-O-benzyl-D-glucal, see R. A. Alonso, G. D. Vite, R. E. McDevitt, B. Fraser-Reid, J. Org. Chem. 1992, 57, 573-584.
35. The analytical data for oxazoline 9 was found to be identical in all respects to that previously reported. See: A. Vasella, C. Witzig, Helv. Chim. Acta 1995, 78, 1971-1982.
36. The gluco-oxazolines 11 and 12 were each isolated as diastereomeric mixtures containing minor amounts of their corresponding manno-oxazoline stereoisomers in diastereomeric ratios of 9:1 and 10:1, respectively.
37. 3N-neutralized silica gel to minimize oxazoline hydrolysis.