Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3)

Carbohydrate Research

Volumn 341, Issue 10, 2006, Pages 1458-1466

  Pornsuriyasak, Papapida ^a   Demchenko, Alexei V ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

Convergent strategy; Glycosylation; Selective activation; Stereoselective synthesis

Indexed keywords

ANTIGENS; CARBOHYDRATES; ONCOLOGY; STEREOCHEMISTRY;

CONVERGENT STRATEGY; GLYCOSYLATION; SELECTIVE ACTIVATION; STEREOSELECTIVE SYNTHESIS;

SYNTHESIS (CHEMICAL);

STAGE SPECIFIC EMBRYO ANTIGEN 3; THIAZOLE DERIVATIVE; TUMOR ANTIGEN;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

ANTIGENS, TUMOR-ASSOCIATED, CARBOHYDRATE; GLYCOSPHINGOLIPIDS; STEREOISOMERISM; THIAZOLES;

EID: 33646908636     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.03.041     Document Type: Article

References (38)

1. Hakomori S. Acta Anat. 161 (1998) 7990
2. Danishefsky S.J., and Allen J.R. Angew. Chem., Int. Ed. 39 (2000) 836-863
3. Boons G.J. Tetrahedron 52 (1996) 1095-1121
4. Demchenko A.V. Lett. Org. Chem. 2 (2005) 580-589
5. Seeberger P.H., and Haase W.C. Chem. Rev. 100 (2000) 4349-4393
6. Koeller K.M., and Wong C.H. Chem. Rev. 100 (2000) 4465-4493
7. Plante O.J., Palmacci E.R., and Seeberger P.H. Science 291 (2001) 1523-1527
8. Nunomura S., and Ogawa T. Tetrahedron Lett. 29 (1988) 5681-5684
9. Nilsson U., and Magnusson G. Carbohydr. Res. 272 (1995) 9-16
10. Park T.K., Lim I.J., and Danishefsky S.J. Tetrahedron Lett. 36 (1995) 9089-9092
11. Bosse F., Marcaurelle L.A., and Seeberger P.H. J. Org. Chem. 67 (2002) 6659-6670
12. Bilodeau M.T., Park T.K., Hu S., Randolph J.T., Danishefsky S.J., Livingston P.O., and Zhang S. J. Am. Chem. Soc. 117 (1995) 7840-7841
13. Lassaletta J., and Schmidt R.R. Liebigs Ann. (1996) 1417-1423
14. Zhu T., and Boons G.J. Angew. Chem., Int. Ed. 38 (1999) 3495-3497
15. Burkhart F., Zhang A., Wacowich-Sgarbi S., and Wong C.H. Angew. Chem., Int. Ed. 40 (2001) 1274-1277
16. Ishida H., Miyawaki R., Kiso M., and Hasegawa A. J. Carbohydr. Chem. 15 (1996) 163-182
17. Lassaletta J.M., Carlsson K., Garegg P.J., and Schmidt R.R. J. Org. Chem. 61 (1996) 6873-6880
18. Demchenko A.V., Pornsuriyasak P., De Meo C., and Malysheva N.N. Angew. Chem., Int. Ed. 43 (2004) 3069-3072
19. Demchenko A.V., and Boons G.J. J. Org. Chem. 66 (2001) 2547-2554
20. Chernyak A.Y., Sharma G.V.M., Kononov L.O., Krishna P.R., Levinsky A.B., Kochetkov N.K., and Rao A.V.R. Carbohydr. Res. 223 (1992) 303-309
21. Demchenko, A. V.; Pornsuriyasak, P.; De Meo, C. J. Chem. Educ., in press.
22. Garegg P.J. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel Dekker, New York 53-67
23. Demchenko A.V. Curr. Org. Chem. 7 (2003) 35-79
24. Pornsuriyasak, P.; Kamat, M. N.; Demchenko, A. V. ACS Symp. Ser., in press.
25. Pornsuriyasak, P.; Demchenko, A. V., submitted for publication.
26. Dullenkopf W., Castro-Palomino J.C., Manzoni L., and Schmidt R.R. Carbohydr. Res. 296 (1996) 135-147
27. Ellervik U., and Magnusson G. Carbohydr. Res. 280 (1996) 251-260
28. Fraser-Reid B., Udodong U.E., Wu Z.F., Ottosson H., Merritt J.R., Rao C.S., Roberts C., and Madsen R. Synlett (1992) 927-942 and references cited therein
29. Helferich B., and Wedermeyer K.F. Ann. 563 (1949) 139-145
30. Ellervik U., and Magnusson G. Tetrahedron Lett. 38 (1997) 1627-1628
31. Nukada T., Berces A., and Whitfield D.M. J. Org. Chem. 64 (1999) 9030-9045
32. Pornsuriyasak P., and Demchenko A.V. Tetrahedron: Asymmetry 16 (2005) 433-439
33. Crich D., and Dudkin V. J. Am. Chem. Soc. 123 (2001) 6819-6825 and references cited therein
34. Spijker N.M., and van Boeckel C.A.A. Angew. Chem., Int. Edit. Engl. 30 (1991) 180-183
35. Demchenko A.V., and De Meo C. Tetrahedron Lett. 43 (2002) 8819-8822
36. Demchenko A.V., and Boons G.J. Tetrahedron Lett. 39 (1998) 3065-3068
37. Lemieux R.U., and Kondo T. Carbohydr. Res. 35 (1974) C4-C6
38. Kochetkov N.K., Klimov E.M., Malysheva N.N., and Demchenko A.V. Carbohydr. Res. 212 (1991) 77-91