N-p-nitrobenzyloxycarbonyl galactosamine imidate as a glycosyl donor for the efficient synthesis of mucin core-2 analogue

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 8, 2000, Pages 793-795

  Liao, Wensheng ^a   Piskorz, Conrad F ^a   Locke, Robert D ^a   Matta, Khushi L ^a  

^a Roswell Cancer Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBOHYDRATE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS; SYNTHESIS;

CARBOHYDRATE SEQUENCE; GALACTOSAMINE; MOLECULAR SEQUENCE DATA; MUCINS; NITROBENZENES;

EID: 0034678649     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00107-4     Document Type: Article

References (20)

1. (a) Chandrasekaran, E. V.; Jain, R. K.; Vig, R.; Matta, K. L. Glycobiology 1997, 7, 753;
2. (b) Chandrasekaran, E. V.; Matta, K. L. Manuscript in preparation.
3. Chandrasekaran E.V., Jain R.K., Rhodes J.M., Srnka C.A., Larsen R.D., Matta K.L. Biochemistry. 34:1995;4748.
4. Barresi F., Hindsgaul O. J. Carbohydr. Chem. 14(8):1995;1043.
5. (a) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem. Int. Ed. Engl. 1997, 36, 1998;
6. (b) Castro-Palomino, J. C.; Schmidt, R. R. Tetrahedron Lett. 1995, 36, 6871;
7. (c) Ellervik, U.; Magnusson, G. Carbohydr. Res. 1996, 280, 251;
8. (d) Jiao, H.; Hindsgaul, O. Angew. Chem., Int. Ed. Engl. 1999, 38, 346;
9. (e) Debenham, J. S.; Madsen, R.; Robert, C.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 177, 3302.
10. (a) Boullanger, P.; Jouineau, M.; Bouammali, B.; Lafont, D.; Descotes, G. Carbohydr. Res. 1990, 202, 151;
11. (b) Guibe-Jampel, E.; Wakselman, M. Synth. Commun. 1982, 12, 219;
12. (c) For corresponding glucosamine derivative as glycosyl donor, see: Qian, X.; Hindsgaul, O. J. Chem. Soc., Chem. Commun. 1997, 1059.
13. (a) Lemieux, R. U.; Takeda, T.; Chung, B. Y. A.C.S. Symp. Ser. 1976, 39, 90;
14. (b) Spijker, N. M.; Westerduin, P.; van Boeckel, C. A. A. Tetrahedron 1992, 48, 6297;
15. (c) Kanie, O.; Crawley, S. C.; Palcic, M. M.; Hindsgaul, O. Carbohydr. Res. 1993, 243, 139.
16. 2:MeOH) to afford compound 8 (55 mg, 80%).
17. Schmidt R.R. Angew. Chem., Int. Ed. Engl. 25:1986;212.
18. Jain, R. K.; Matta, K. L. manuscript in preparation.
19. Konradsson P., Udodong U.E., Fraser-Reid B. Tetrahedron Lett. 31:1990;4313.
20. 2O, 100.6 MHz) δ 173.53, 173.10, 172.63 (3 CO), 101.68 (C-1″′), 100.82 (C-1′), 100.34 (C-1″), 97.60 (C-1″″), 97.12 (C-1), 54.69 (OMe), 21.29, 21.26, 21.04 (3×NHAc), 14.27 (C-6″″).