Synthesis of D-gluco-, L-ido-, D-galacto-, and L-altro-configured glycaro-1,5-lactams from tartaric acid

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3619-3622

  Pabba, Jagadish ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Carbohydrates; Glycarolactam; Lactam; Synthesis; Tartaric acid

Indexed keywords

ACID ANHYDRIDE; ALDEHYDE; BETA GLUCURONIDASE; CARBOHYDRATE DERIVATIVE; ENZYME INHIBITOR; LACTAM DERIVATIVE; TARTARIC ACID;

ARTICLE; DEPROTECTION REACTION; DIHYDROXYLATION; DRUG POTENCY; DRUG SYNTHESIS; LACTONIZATION; OLEFINATION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION;

EID: 17844382716     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.188     Document Type: Article

References (33)

1. K. Paigen Prog. Nucl. Acid Res. Mol. Biol. 37 1989 155
2. W.S. Sly, B.A. Quinton, Wh. McAliste, and D.L. Rimoin J. Pediatrics 82 1973 249
3. C.W. Hall, M. Cantz, and E.F. Neufeld Arch. Biochem. Biophys. 155 1973 32
4. E.F. Neufeld, and J. Muenzer The Mucopolysaccharidoses C.R. Scriver A.L. Beaudet W.S. Sly The Metabolic Basis of Inherited Disease 7th ed. 1995 McGraw-Hill New York 2465
5. D.A. Brooks, G.S. Harper, G.J. Gibson, L.J. Ashton, J.A. Taylor, P.A.G. McCourt, C. Freeman, P.R. Clements, J.W. Hoffmann, and J.J. Hopwood Biochem. Med. Metab. Biol. 47 1992 211
6. N. Kinoshita, and H.V. Gelboin Science 199 1978 307
7. D.H. Kim, H.J. Kang, S.H. Park, and K. Kobashi Biol. Pharm. Bull. 17 1994 423
8. J.C. Caygill, and D.A. Pitkeathy Ann. Rheum. Dis. 25 1966 137
9. G. Weissman, R.B. Zurier, P.J. Spieler, and I.M. Goldstein J. Exp. Med. 134 1971 S149
10. For some recent references, see: T.D. Heightman, and A.T. Vasella Angew. Chem., Int. Ed. 38 1999 750
11. A. Vasella, G.J. Davies, and M. Böhm Curr. Opin. Chem. Biol. 6 2002 619
12. M. Böhm, E. Lorthiois, M. Meyyappan, and A. Vasella Helv. Chim. Acta 86 2003 3818
13. T.M. Gloster, S.J. Williams, S. Roberts, C.A. Tarling, J. Wicki, S.G. Withers, and G.J. Davies Chem. Commun. 2004 1794
14. M. Böhm, and A. Vasella Helv. Chim. Acta 87 2004 2566
15. F. Vincent, T.M. Gloster, J. Macdonald, C. Morland, R.V. Stick, F.M.V. Dias, J.A.M. Prates, C. Fontes, H.J. Gilbert, and G.J. Davies Chembiochem 5 2004 1596
16. T.M. Gloster, J.M. Macdonald, C.A. Tarling, R.V. Stick, S.G. Withers, and G.J. Davies J. Biol. Chem. 279 2004 49236
17. M. Terinek, and A. Vasella Helv. Chim. Acta 87 2004 3035
18. N. Mohal, and A. Vasella Helv. Chim. Acta 88 2005 100
19. T. Niwa, T. Niida, T. Tsuruoka, S. Inouye, T. Koeda, and Y. Naito J. Biochem. (Tokyo) 72 1972 207
20. S. Guntha, and H.B. Mereyala Tetrahedron Lett. 35 1994 4869
21. J. Gawronski, and K. Gawronska Tartaric and Malic Acids in Synthesis: A Source Book of Building Blocks, Ligands, Auxiliaries, and Resolving Agents 1998 John Wiley & Sons
22. A.K. Ghosh, E.S. Koltun, and G. Bilcer Synthesis 2001 1281
23. H. Iida, N. Yamazaki, and C. Kibayashi J. Org. Chem. 52 1987 3337
24. H. Ina, and C. Kibayashi J. Org. Chem. 58 1993 52
25. G. Pandey, M. Kapur, M.I. Khan, and S.M. Gaikwad Org. Biomol. Chem. 1 2003 3321
26. W.W. Lee, and S. Chang Tetrahedron: Asymmetry 10 1999 4473
27. R.M. Conrad, M.J. Grogan, and C.R. Bertozzi Org. Lett. 4 2002 1359
28. J. Ohwada, Y. Inouye, M. Kimura, and H. Kakisawa Bull. Chem. Soc. Jpn. 63 1990 287
29. L. De Luca, G. Giacomelli, and A. Porcheddu Org. Lett. 3 2001 3041
30. U. Schmidt, H. Griesser, V. Leitenberger, A. Lieberknecht, R. Mangold, R. Meyer, and B. Riedl Synthesis 1992 487
31. R. Wagner, J.W. Tilley, and K. Lovey Synthesis 1990 785
32. J.K. Cha, W.J. Christ, and Y. Kishi Tetrahedron 40 1984 2247
33. J.S. Brimacombe, R. Hanna, and F. Bennett Carbohydr. Res. 135 1985 C17