Thiazolylketol acetates as glycosyl donors. Stereoselective synthesis of α-linked ketodisaccharides

Tetrahedron

Volumn 52, Issue 9, 1996, Pages 3057-3074

  Dondoni, Alessandro ^a   Marra, Alberto ^a   Rojo, Isabel ^a   Scherrmann, Marie Christine ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030022998     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01095-5     Document Type: Article

References (50)

1. (a) Dondoni, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7319;
2. (b) Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404.
3. Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517.
4. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
5. Müller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763.
6. (a) Heskamp, B. M.; Noort, D.; van der Marel, G. A.; van Boom, J. H. Synlett 1992, 713;
7. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 5657.
8. For other syntheses of ketosides via enol ethers see: (a) Ikeda, K.; Akamatsu, S.; Achiwa, K. Carbohydr. Res. 1989, 189, C1;
9. (b) Thiem, J.; Kleeberg, M. Carbohydr. Res. 1990, 205, 333;
10. (c) Haudrechy, A.; Sinaÿ, P. J. Org. Chem. 1992, 57, 4142.
11. Nicotra, F.; Panza, L.; Russo, G. Tetrahedron Lett. 1991, 32, 4035.
12. Lay, L.; Nicotra, F.; Panza, L.; Russo, G. Synlett 1995, 167.
13. Eby, R.; Schuerch, C. Carbohydr. Res. 1974, 34, 79. Compound 3 was prepared according to: Lipták, A.; Jodál, I.; Nánási, P. Carbohydr. Res. 1974, 44, 1.
14. Eby, R.; Schuerch, C. Carbohydr. Res. 1974, 34, 79. Compound 3 was prepared according to: Lipták, A.; Jodál, I.; Nánási, P. Carbohydr. Res. 1974, 44, 1.
15. 13C-NMR experiments. Thus, the configuration was assigned through the corresponding methyl ester derivatives 4d, 8d, 9d, and 10d on the basis of the vicinal coupling constants between the carboxyl carbon C-1′ and the axial proton H-3′ (ulosonic acid numbering) following a rule established for sialic acids (Haverkamp, J.; Spoormaker, T.; Dorland, L.; Vliegenthart, J. F. G.; Schauer, R. J. Am. Chem. Soc. 1979, 101, 4851)
16. and sialic acid methyl esters (Hori, H.; Nakajima, T. Nishida, Y.; Ohrui, H.; Meguro, H. Tetrahedron Lett. 1988, 29, 6317;
17. 1 conformation having nearly 60° and 180° dihedral angles C-1-C-2-C-3-H-3, respectively. In each series, the stereochemistry assigned to esters was assumed for their precursors as well.
18. The intermediacy of α-nitrilium ions by use of acetonitrile or propionitrile as the solvents is well established, see: Braccini, I.; Derouet, C.; Esnault, J.; Hervé du Penhoat, C.; Mallet, J.-M.; Michon, V.; Sinay, P. Carbohydr. Res. 1993, 246, 23 and references cited therein.
19. Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370.
20. Küster, J. M.; Dyong, I. Liebigs, Ann. Chem. 1975, 2179. Compound 5 was prepared according to: Mallet, J.-M.; Meyer, G.; Yvelin, F.; Jutand, A.; Amatore, C.; Sinay, P. Carbohydr. Res. 1993, 244, 237.
21. Küster, J. M.; Dyong, I. Liebigs, Ann. Chem. 1975, 2179. Compound 5 was prepared according to: Mallet, J.-M.; Meyer, G.; Yvelin, F.; Jutand, A.; Amatore, C.; Sinay, P. Carbohydr. Res. 1993, 244, 237.
22. When this glycosidation was carried out in the presence of 1 equiv of TMSOTf the disaccharide 8a was recovered in -55% yield. The efficiency of the so-called "inverse procedure" has been already proven using trichloroacetimidate derivatives as glycosyl donors (Schmidt, R. R.; Toepfer, A. Tetrahedron Lett. 1991, 32, 3353).
23. The α-configuration of the furanose thiazolylketodisaccharides 11a and 12a was assigned by NOESY experiments showing enhancements between H-4′ and H-6b (for 11a), H-4′ and H-3, H-2′ and H-4 (for 12a).
24. Lewis acid-promoted glycosidation of 1-O-acetyl-aldofuranose and -aldopyranose derivatives has been reported. See: Mukaiyama, T.; Takashima, T.; Katsurada, M.; Aizawa, H. Chem. Lett. 1991, 533 and previous papers cited therein.
25. Noyce, D. S.; Fike, S. D. J. Org. Chem. 1973, 38, 3316.
26. 1H-NMR spectra of the thiazolylketoside 13 and the methyl ester (α)-15 showed chemical shifts and coupling constants values similar to those displayed by the corresponding α-thiazolylketol (see product 3e in réf. 1b) and the methyl ester (α)-18 (see Experimental), respectively. This allowed to assign the α-configuration to 13 and (α)-15.
27. C-1 values (downfield chemical shifts have been reported for the ketofuranose anomers having the C-1-O-1 and C-2-O-2 bonds in a trans orientation; see: ref. 1b and Boschetti, A.; Panza, L.; Ronchetti, F.; Russo, G.; Toma, L. J. Chem. Soc. Perkin Trans. I 1988, 3353). The anomeric configuration of the thermodynamic acetate (α)-18 and the kinetic anomer (β)-18 was determined by the same method.
28. C-1 values (downfield chemical shifts have been reported for the ketofuranose anomers having the C-1-O-1 and C-2-O-2 bonds in a trans orientation; see: ref. 1b and Boschetti, A.; Panza, L.; Ronchetti, F.; Russo, G.; Toma, L. J. Chem. Soc. Perkin Trans. I 1988, 3353). The anomeric configuration of the thermodynamic acetate (α)-18 and the kinetic anomer (β)-18 was determined by the same method.
29. Although it is quite obvious, this result clearly demonstrates that the intermediate oxycarbenium ion generated from donors bearing a carboxymethyl function is not stabilised by conjugation with the carbonyl oxygen. An opposite conclusion has been reported by others. See: Kirchner, E.; Thiem, F.; Demick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem. 1988, 7, 453.
30. 1H-NMR spectra of the ketodisaccharides 19 and 21 showed chemical shifts and coupling constants values similar to those displayed by the ketol (α)-17 and the thiazolylketodisaccharide 11a (see Experimental), respectively. This allowed to assign the α-configuration to 19 and 21.
31. For reviews concerning the glycosidation of variously activated sialyl donors see: (a) Okamoto, K.; Goto, T. Tetrahedron 1990, 46, 5835;
32. (b) DeNinno, M. P. Synthesis 1991, 583. See also:
33. (a) Lönn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115;
34. (b) Martin T. J.; Schmidt R. R. Tetrahedron Lett. 1992, 33, 6123;
35. (c) Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glyconjugate J. 1993, 10, 16;
36. (d) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864.
37. The addition of 2-lithiofuran (prepared according to: Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265) to the sugar lactone 16 gave an anomeric mixture of 1-C-(2-furyl)-D-mannofuranose derivative 20 (70%) which, on treatment with acetic anhydride and triethylamine, afforded the crude anomeric acetates. However, upon purification on silica gel column the extremely acid sensitive 1-O-acetyl-1-C-(2-furyl)-2,3:5,6-di-O-isopropylidene-α,β-D- mannofuranose hydrolysed completely to afford 20. 24. (a) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280.
38. The addition of 2-lithiofuran (prepared according to: Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265) to the sugar lactone 16 gave an anomeric mixture of 1-C-(2-furyl)-D-mannofuranose derivative 20 (70%) which, on treatment with acetic anhydride and triethylamine, afforded the crude anomeric acetates. However, upon purification on silica gel column the extremely acid sensitive 1-O-acetyl-1-C-(2-furyl)-2,3:5,6-di-O-isopropylidene-α,β-D- mannofuranose hydrolysed completely to afford 20. 24. (a) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280.
39. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929.
40. Dondoni, A.; Marra, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323.
41. A tempting hypothesis can be advanced wherein the anchimeric assistance of the thiazole ring favours the formation of the oxycarbenium II through the intermediate I (E = Lewis acid). matrix presented
42. 2/CuO are only partially hydrolysed to aldehyde.
43. Yamada, S.; Morizono, D.; Yamamoto, K. Tetrahedron Lett. 1992, 33, 4329.
44. The thiazolylketodisaccharides 9a and 10a were converted only into aldehydes 9b-10b and methyl esters 9d-10d. 30. (a) Noort, D.; van Straten, N. C. R.; Boons, G. J. P. H.; van der Marel, G. A.; Bossuyt, X.; Blanckaert, N.; Mulder, G. J.; van Boom, J. H. Bioorg. Med. Chem. Lett. 1992, 2, 583.
45. (b) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397.
46. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
47. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
48. Horton, D.; Jewell, J. S. Carbohydr. Res. 1966, 2, 251.
49. Schmidt, O. T. Methods Carbohydr. Chem. 1963, 2, 318.
50. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647.