A short synthetic route to β-C-glycosides of N-acetylglucosamine

Synlett

Volumn , Issue 7, 2006, Pages 1004-1008

  Rat, Stéphanie ^a   Norsikian, Stéphanie ^a  

^a CNRS   (France)

Author keywords

Aldehydes; Carbohydrates; Enols; Glycosides; Oxidations

Indexed keywords

1 C (2 N ACETAMIDO 2 DEOXY 3,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL)PROPAN 2 ONE; ACETONE; BENZALDEHYDE; BETA C GLYCOSIDE DERIVATIVE; GLYCOSIDE; KETONE; N ACETYLGLUCOSAMINE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33646587390     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939061     Document Type: Article

References (38)

1. (a) Hanessian, S. In Total Synthesis of Natural Products: The Chiron Approach; Pergamon: New York, 1983.
2. (b) BeMiller, J. N.; Yadav, M. P.; Kalabokis, V. N.; Myers, R. W. Carbohydr. Res. 1990, 200, 111.
3. (c) Schmidt, R. R.; Dietrich, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1328.
4. (d) Nicotra, F. Top. Curr. Chem. 1997, 187, 55.
5. (e) Wang, J.; Kovác, P.; Sinaÿ, P.; Glaudemans, C. P. J. Carbohydr. Res. 1998, 308, 191.
6. (f) Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384.
7. (a) Jimenez-Barbero, J.; Espinosa, J. F.; Asensio, J. L.; Canada, F. J.; Poveda, A. Adv. Carbohydr. Chem. Biochem. 2001, 56, 235.
8. (b) Asensio, J. L.; Cañada, F. J.; Cheng, X.; Khan, N.; Mootoo, D. R.; Jimenez-Barbero, J. Chem. Eur. J. 2000, 6, 1035.
9. (a) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales-Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639.
10. (b) Xin, Y.-C.; Zhang, Y.-M.; Mallet, J.-M.; Glaudemans, C. P. J.; Sinaÿ, P. Eur. J. Org. Chem. 1999, 471.
11. (c) Wellner, E.; Gustafsson, T.; Bäcklund, J.; Holmdahl, R.; Kihlberg, J. ChemBioChem 2000, 1, 272.
12. (d) Yang, G.; Franck, R. W.; Bittmann, R.; Samadder, P.; Arthur, G. Org. Lett. 2001, 3, 197.
13. (e) Mikkelsen, L. M.; Hernáiz, M. J.; Martín-Pastor, M.; Skrydstrup, T.; Jimenez-Barbero, J. J. Am. Chem. Soc. 2002, 124, 14940.
14. (f) Schmieg, J.; Yang, G.; Franck, R. W.; Tsuji, M. J. Exp. Med. 2003, 198, 1631.
15. (g) Yang, G.; Schmieg, J.; Tsuji, M.; Franck, R. W. Angew. Chem. Int. Ed. 2004, 43, 3818.
16. (h) Chaulagain, M. R.; Postema, M. H. D.; Valeriote, F.; Pietraszkewicz, H. Tetrahedron Lett. 2004, 45, 7791.
17. (a) Varki, A. Glycobiology 1993, 3, 97.
18. (b) Dwek, R. A. Chem. Rev. 1996, 96, 68.
19. (a) Postema, M. H. D. In C-Glycoside Synthesis, Rees, C. W., Ed.; CRC Press: Boca Raton, 1995, 193.
20. (b) Du, Y.; Linhart, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913.
21. (c) Beau, J. M.; Vauzeilles, B.; Skrydstrup, T. In Glycoscience III; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer: Berlin, 2001, 2679.
22. (a) Bertozzi, C. R.; Bednarski, M. D. Tetrahedron Lett. 1992, 22, 3109.
23. (b) Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 604.
24. (c) Petrusová, M.; BeMiller, J. N.; Krihová, A.; Petrus, L. Carbohydr. Res. 1996, 295, 57.
25. (d) Gaurat, O.; Xie, J.; Valéry, J.-M. J. Carbohydr. Chem. 2003, 22, 645.
26. (e) McGarvey, G. J.; Schmidtmann, F. W.; Benedum, T. E.; Kizer, D. E. Tetrahedron Lett. 2003, 44, 3775.
27. Zeitouni, J.; Norsikian, S.; Lubineau, A. Tetrahedron Lett. 2004, 45, 7761.
28. Bragnier, N.; Scherrmann, M.-C. Synthesis 2005, 814.
29. 10N: C, 53.14; H, 6.34; O, 37.26; N, 3.26. Found: C, 52.97; H, 6.27; O, 37.34; N, 3.12.
30. Prepared according to: Adam, W.; Bialas, J.; Hadjiarapoglou, E. Chem. Ber. 1991, 124, 2377.
31. 3: C, 63.55; H, 6.63; O, 37.26; N, 6.74. Found: C, 63.93; H, 6.81; N, 6.53.
32. 3).
33. Burk, M. J.; Allen, J. G. J. Org. Chem. 1997, 62, 7054.
34. 3: C, 64.01; H, 6.76; O, 22.01; N, 7.22. Found: C, 63.84; H, 7.06; O, 22.09; N, 6.88.
35. 3).
36. 3: C, 76.11; H, 7.08; O, 11.02; N, 5.79. Found: C, 76.02; H, 6.83; N, 5.76.
37. 3).
38. 10N: C, 54.17; H, 6.59; O, 36.08; N, 3.16. Found: C, 53.72; H, 6.64; N, 3.06.