A convenient synthesis of alkyl D-glycofuranosiduronic acids and alkyl D-glycofuranosides from unprotected carbohydrates

Carbohydrate Research

Volumn 311, Issue 1-2, 1998, Pages 25-35

  Ferrières, Vincent ^a   Bertho, Jean Noël ^a   Plusquellec, Daniel ^a  

^a CNRS   (France)

Author keywords

Alkyl D glycofuranosides; Alkyl D glycofuranosiduronic acids; Glycosylation; Unprotected carbohydrates

Indexed keywords

CARBOHYDRATE; TETRAHYDROFURAN; URONIC ACID;

ARTICLE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CRYSTALLIZATION; DRUG SYNTHESIS; GLYCOSYLATION; METHODOLOGY; NONHUMAN; PRIORITY JOURNAL;

EID: 0343121726     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00197-9     Document Type: Article

References (31)

1. (a) R.R. Schmidt, Angew. Chem., Int. Ed. Engl., 25 (1986) 212-235;
2. (b) R.R. Schmidt, in B.M. Trost, I. Fleming, and E. Winterfeld (Eds.), Comprehensive Organic Synthesis, Vol. 6, Pergamon Press, New York, 1991, pp 33-64;
3. (c) K. Toschima and K. Tatsuta, Chem. Rev., 93 (1993) 1503-1531;
4. (d) G.J. Boons, Tetrahedron, 52 (1996) 1095-1121.
5. E. Fischer, Ber. Dtsch. Chem. Ges., 26 (1893) 2406-2420.
6. D. Keglevic, Adv. Carbohydr. Chem. Biochem., 36 (1979) 57-134.
7. (a) J.N. Bertho, V. Ferrières, and D. Plusquellec, J. Chem. Soc., Chem. Commun., (1995) 1391-1393;
8. (b) V. Ferrières, J.N. Bertho, and D. Plusquellec, Tetrahedron Lett., 36 (1995) 2749-2752.
9. H.W.C. Raijsmakers, B. Zwanenburg, and G.J.F. Chittenden, Recl. Trav. Chim. Pays Bas, 113 (1994) 79-87.
10. (a) C.S. Hudson, J. Am. Chem. Soc., 31 (1909) 66-86;
11. (b) S.J. Angyal, Carbohydr. Res., 77 (1979) 37-50.
12. K. Dax and H. Weidmann, Adv. Carbohydr. Chem. Biochem., 33 (1976) 189-234.
13. (a) E.F. Jansen and R. Jang, J. Am. Chem. Soc., 68 (1946) 1475-1477;
14. (b) K. Larsson and G. Petersson, Carbohydr. Res., 34 (1974) 323-329;
15. (c) J. Vlahov and G. Snatzke, Liebigs Ann. Chem., (1983) 570-574.
16. (a) S.J. Farber, M. Schubert, and M. Schuster, J. Clin. Invest., 36 (1957) 1715-1722;
17. (b) R.S. Turner and M.M. Burger, Nature, 244 (1973) 509-510;
18. (c) G. Weinbaum and M.M. Burger, Nature, 244 (1973) 510-512.
19. (a) K. Bock and C. Pedersen, Adv. Carbohydr. Chem. Biochem., 41 (1983) 27-66;
20. (b) B. Matsuhiro, A.B. Zanlungo, and G.G.S. Dutton, Carbohydr. Res., 97 (1981) 11-18.
21. A. Lubineau and J.C. Fischer, Synth. Commun., 21 (1991) 815-818.
22. (a) M.E. Evans and S.J. Angyal, Carbohydr. Res., 25 (1972) 43-48;
23. (b) S.J. Angyal, Chem. Soc. Rev., 9 (1980) 415-428 and references therein.
24. R.G.S. Ritchie, N. Cyr, B. Korsch, H.J. Koch, and A.S. Perlin, Can. J. Chem., 53 (1975) 1424-1433.
25. W. Klotz and R.R. Schmidt, Liebigs Ann. Chem., (1993) 683-690.
26. (a) J.W. Goodby, J.A. Haley, G. Mackenzie, M.J. Watson, D. Plusquellec, and V. Ferrières, J. Mater. Chem., 5 (1995) 2209-2220;
27. (b) X. Auvray, B. Labulle, C. Petipas, J.N. Bertho, T. Benvegnu, and D. Plusquellec, J. Mater. Chem., 7 (1997) 1373-1376;
28. (c) L.F. Tietze, K. Böge, and V. Vill, Chem. Ber., 127 (1994) 1065-1068.
29. R. Velty, T. Benvegnu, M. Gelin, E. Privat, and D. Plusquellec, Carbohydr. Res., 299 (1997) 7-14.
30. M. Gelin, V. Ferrières, and D. Plusquellec, Carbohydr. Lett., 2 (1997) 381-388.
31. W.V. Dahlhoff, Synthesis, (1987) 366-368.