N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective α-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation

Journal of the American Chemical Society

Volumn 128, Issue 33, 2006, Pages 10666-10667

  Manabe, Shino ^a,b   Ishii, Kazuyuki ^b   Ito, Yukishige ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; HEPARIN; N BENZYL 2,3 OXAZOLIDINONE; OLIGOSACCHARIDE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; THROMBOEMBOLISM;

EID: 33747799654     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062531e     Document Type: Article

References (25)

1. For reviews of 1,2-cis glycosylation: (a) Demchenko, A. V. Curr. Org. Chem. 2003, 7, 35-79.
2. (b) Demchenko, A. V. Synlett 2003, 1225-1240.
3. (c) Fairbanks, A. J. Synlett 2003, 1945-1858.
4. (a) Paulsen, H.; Kalar, C.; Stenzel, W. Chem. Ber. 1978, 111, 2358-2369.
5. (b) Lemieux, R. U.; Ratcliffe, R. M. Can. J. Chem. 1979, 57, 1244-1251.
6. (c) For review of synthesis of oligosaccharides of 2-amino-2-deoxy sugars: Banoub, J.; Baullanger, P.; Lafont, D. Chem. Rev. 1992, 92, 1167-1195.
7. Benakli, K.; Zha, C.; Kerns, R. J. J. Am. Chem. Soc. 2001, 123, 9461-9462.
8. (a) Kerns, R. J.; Zha, C.; Benakli, K.; Liang, Y.-Z. Tetrahedron Lett. 2003, 44, 8069-8072.
9. (b) Wei, P.; Kerns, R. J. J. Org. Chem. 2005, 70, 4195-4198.
10. (c) Wei, P.; Kerns, R. J. Tetrahedron Lett. 2005, 46, 6901-6905.
11. (a) Crich, D.; Vinod, A. U. J. Org. Chem. 2005, 70, 1291-1296.
12. (b) Boysen, M.; Gemma, E.; Lahmann, M.; Oscarson, S. Chem. Commun. 2005, 3044-3046.
13. Crich, D.; Sun, S. J. Am. Chem. Soc. 1998, 120, 435-436.
14. Duron, S. G.; Polat, T.; Wong, C.-H. Org. Lett. 2004, 6, 839-841.
15. The ratios of stereochemistry were determined kinetically. The β-compound was not converted to the corresponding α-isomer under the glycosylation reaction conditions.
16. Demchenko, A. V.; Stauchi, T.; Boons, G.-J. Synlett 1997, 818-820.
17. When the azido donor, as indicated below, was coupled to 12 under condition B at -40 °C, both áand β glycosides were obtained in 24% and 10%, respectively, (diagram presented).
18. (a) Orgueira, H. A.; Bartolozzi, P. S.; Schell, P.; Seeberger, P. H. Angew. Chem., Int. Ed. 2002, 41, 2128-2131.
19. (b) Lohman, G. J. S.; Hunt, D. K.; Högermeier, J. A.; Seeberger, P. H. J. Org. Chem. 2003, 68, 7559-7561.
20. For a recent review for heparin: Noti, C.; Seeberger, P. H. Chem. Biol. 2005, 12, 731-756.
21. (a) Koeller, K. M.; Wong, C.-H. Chem. Rev. 2000, 100, 4465-4493.
22. (b) Boons reported the preparation of trisaccharides with 1″,2″-trans and 1′,2′-cis glycosidic linkage sequences in a one-pot procedure: Zhu, T.; Boons, G.-J. Org. Lett. 2001, 3, 4201-4203.
23. Bartodziejska, B.; Toukach, F. V.; Vinogradov, E. V.; Senchenkova, S. N.; Shashkov, A. S.; Ziolkowski, A.; Czaja, J.; Perry, M. B.; Knirel, Y. A.; Rozalski, A. Eur. J. Biochem. 2000, 267, 6888-6896.
24. (a) Ito, Y.; Manabe, S. Chem.-Eur. J. 2002, 8, 3086-3084.
25. (b) Seeberger, P. H.; Werz, D. B. Nat. Rev. Drug Discovery 2005, 4, 751-763.