A fused GalNAc-thiazole from a singular and unanticipated fragmentation

Tetrahedron Letters

Volumn 45, Issue 46, 2004, Pages 8507-8510

  Knapp, Spencer ^a   Amorelli, Benjamin ^a   A Doss, George ^b  

^a RUTGERS UNIVERSITY   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Aromatization; Rearrangement; Retro aldol

Indexed keywords

ENZYME INHIBITOR; ESTER DERIVATIVE; ETHER DERIVATIVE; N ACETYLGALACTOSAMINE THIAZOLE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DESILYLATION; DRUG SYNTHESIS; FRAGMENTATION REACTION; REACTION ANALYSIS;

EID: 5644224478     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.091     Document Type: Article

References (14)

1. B.L. Mark, D.J. Mahuran, M.M. Cherney, D. Zhao, S. Knapp, and M.N.G. James J. Mol. Biol. 327 2003 1093 1109
2. S. Knapp, C. Yang, and T. Haimowitz Tetrahedron Lett. 43 2002 7101 7104
3. J.L. Koviach, M.D. Chappell, and R.L. Halcomb J. Org. Chem. 66 2001 2318 2326
4. S. Czernecki, and E. Ayadi Can. J. Chem. 73 1995 343 350
5. J. Xie, A. Molina, and S. Czernecki J. Carbohydr. Chem. 18 1999 481 498
6. 1H NMR signal for the thiazoline methyl of 8 at 2.17 ppm (br s, long range coupled to H-2) is diagnostic: S. Knapp, and D.S. Myers J. Org. Chem. 67 2002 2995 2999 The thioacetamide methyl singlet of 9, observed at 2.47 ppm, is also diagnostic, and integration gives their ratio. Complete spectra are given in Ref. 14
7. The closest analogous non-aromatized structure is the corresponding GalNac-thiazoline (Ref. 6). Analogous benzo-fused glycals have also been synthesized: K. Pachamuthu, and R.R. Schmidt Synlett 2003 1355 1357
8. The thermal reversion of glyconolactone-thiazole adducts back to the glyconolactones has been observed: A. Dondoni, and A. Marra Heterocycles 50 1999 419 426
9. The corresponding acetamido lactone has been reported: V. Zsoldos-Mady, I. Pinter, A. Nesmelyi, and A. Messmer Carbohydr. Res. 252 1994 85 95
10. D. Horton, J.K. Thomson, O. Varela, A. Nin, and R.M. de Lederkremer Carbohydr. Res. 193 1989 49 60
11. M. Bierenstiel, and M. Schlaf Eur. J. Org. Chem. 2004 1474 1481
12. N. Pravdic, and H.G. Fletcher Jr. Carbohydr. Res. 12 1970 471 474
13. M. Adiyaman, J.A. Lawson, S.-W. Hwang, S.P. Khanapure, G.A. FitzGerald, and J. Rokach Tetrahedron Lett. 37 1996 4849 4852
14. M.S. Motawia, C.E. Olsen, K. Denyer, A.M. Smith, and B.L. Moller Carbohydr. Res. 56 2001 6511 6516