Preparation of polyhydroxyalkyl- and C-glycosylfuran derivatives from free sugars catalyzed by cerium(III) chloride in aqueous solution: An improvement of the Garcia González reaction

Carbohydrate Research

Volumn 339, Issue 7, 2004, Pages 1381-1387

  Misra, Anup Kumar ^a   Agnihotri, Geetanjali ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

C glycoside derivatives; Cerium(III) chloride; Furan

Indexed keywords

CERIUM COMPOUNDS; ESTERS; SOLUTIONS;

1,3-DIONES; ALDOSE SUGARS; MILD NEUTRAL REACTION;

SUGARS;

3 ACETYL 2 METHYL 5 (1,2,3 TRIACETOXYPROPYL)FURAN; 3 ACETYL 5 [3 O ACETYL 1,4 ANHYDRO 2 O (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) BETA DEXTRO ERYTHRO TETROFURANOSYL] 2 METHYLFURAN; 3 ACETYL 5 C (2,3 DI O ACETYL 1,4 ANHYDRO BETA DEXTRO ERYTHRO TETROFURANOSYL) 2 METHYLSULFURAN; 3 ACETYL 5 C (2,3 DI O ACETYL 1,4 ANHYDRO BETA DEXTRO THREO TETROFURANOSYL) 2 METHYLFURAN; 3 ACETYL[3 O ACETYL 1,4 ANHYDRO 2 O (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO ERYTHRO TETROFURANOSYL] 2 METHYLFURAN; CARBOHYDRATE DERIVATIVE; CERIUM; CHLORIDE; ESTER DERIVATIVE; ETHYL 2 METHYL 5 (1,2,3 TRIACETOXYPROPYL) 3 FURANOATE; ETHYL 5 [3 O ACETYL 1,4 ANHYDRO 2 O (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) BETA DEXTRO ERYTHRO TETROFURANOSYL] 2 METHYL 3 FURANOATE; ETHYL 5 [3 O ACETYL 1,4 ANHYDRO 2 O (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO ERYTHRO TETROFURANOSYL] 2 METHYL 3 FURANOATE; ETHYL 5 C (2,3 DI O ACETYL 1,4 ANHYDRO BETA DEXTRO ERYTHRO TETROFURANOSYL) 2 METHYL 3 FURANOATE; ETHYL 5 C (2,3 DI O ACETYL 1,4 ANHYDRO BETA DEXTRO THREO TETROFURANOSYL) 2 METHYL 3 FURANOATE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; DRUG SYNTHESIS; GARCIA GONZALEZ REACTION; METHODOLOGY; PRIORITY JOURNAL;

CARBOHYDRATES; CERIUM; FURANS; GLYCOSIDES; MOLECULAR STRUCTURE; SOLUTIONS;

GARCIA;

EID: 2142760036     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.02.011     Document Type: Article

References (48)

1. Kirshenbaum K., Zuckermann R.N., Dill H.A. Curr. Opin. Struc. Biol. 9:1999;530-535
2. Qiu W., Gu X., Soloshonok V.A., Carducci M.D., Hruby V.J. Tetrahedron Lett. 42:2001;145-148
3. Mowick J.S., Chung D.M., Maitra K., Maitra S., Stigers K.D., Sun Y.J. Am. Chem. Soc. 122:2000;7654-7661
4. Bursavich M.G., Rich D.H. J. Med. Chem. 45:2002;541-558
5. Neilsen P.E. Acc. Chem. Res. 32:1999;624-630
6. Schewizer F. Angew. Chem., Int. Ed. 41:2002;230-253
7. Gruner S.A.W., Truffault V., Voll G., Locardi E., Stockle M., Kessler H. Chem. Eur. J. 8:2002;4365-4376
8. Chakraborty T.K., Jayaprakash S., Srinivasu P., Madhavendra S.S., Ravi Sankar A., Kunwar A.C. Tetrahedron. 58:2002;2853-2859
9. Chakraborty T.K., Ghosh S., Jayaprakash S., Sharma J.A.R.P., Ravikanth V., Diwan P.V., Nagaraj R., Kunwar A.C. J. Org. Chem. 65:2000;6441-6457
10. Long D.D., Smith M.D., Martin A., Wheatley J.R., Watkin D.G., Muller M., Fleet G.W.J. J. Chem. Soc., Perkin Trans. 1. 2002;1982-1998
11. Hungerford N.L., Claridge T.D.W., Watterson M.P., Aplin R.T., Moreno A., Fleet G.W.J. J. Chem. Soc., Perkin Trans. 1. 2000;3666-3679
12. Hungerford N.L., Fleet G.W.J. J. Chem. Soc., Perkin Trans. 1. 2000;3680-3685
13. Smith M.D., Fleet G.W.J. J. Peptide Sci. 5:1999;425-441
14. Chakraborty T.K., Srinivasu P., Kiran Kumar S., Kunwar A.C. J. Org. Chem. 67:2002;2093-2100
15. Crespo L., Sanclimens G., Royo M., Giralt E., Albericio F. Eur. J. Org. Chem. 2002;1756-1762
16. Yoshimoto S., Ichikawa M., Hildreth J.E.K., Ichikawa Y. Tetrahedron Lett. 37:1996;2549-2552
17. Sears P., Wong C.H. Chem. Commun. (Cambridge). 11:1998;1161-1170
18. Cox T., Lachman R., Hollack C., Aerts J., Van Weely S., Hrebicek M., Platt F., Butters T., Dwek R.A., Moyses C., Gow I., Elstein D., Zimran A. Lancet. 355:2000;1481-1485
19. Platt F.M., Reinken-Smeier G., Dwek R.A., Butters T.D. J. Biol. Chem. 272:1997;19365-19372
20. Poeta D.M., Schell W.A., Christine C., Jones S.K., Tidwell R., Kumar A., Baykin D.W., Perfect J.R. Antimicrob. Agents Chemother. 42:1998;2503-2510
21. Lercetto H., Maio D.R., Gonzalez M., Rissao M., Gabriel S., Seoane G., Denicola A., Feluffo G., Quijano C., Stoppani A.O.M. Eur. J. Med. Chem. 35:2000;343-350
22. Setsuyo S., Obase H., Ichikawa S., Kitazawa T., Nonaka H., Yoshizaki R., Ishii A., Shuto K. J. Med. Chem. 36:1993;572-579
23. Daniel J.A., Dave J., Douglas K., Gerry S., Larsen J., Ganiel D., Hongding E., Cohen J., Lee J., Warner R. Bioorg. Med. Chem. Lett. 9:1999;1069-1074
24. Han Y., Giroux A., Lepine C., Laliberte F., Haung Z., Perrier H., Bayly C.I., Young R.N. Tetrahedron. 55:1999;11669-11685
25. Moreno-Vargas A.J., Jimenez-Barbero J., Robina I.J. Org. Chem. 68:2003;4138-4150
26. Moreno-Vargas A.J., Demange R., Fuentes J., Robina I., Vogel P. Bioorg. Med. Chem. Lett. 12:2002;2335-2339
27. Moreno-Vargas A.J., Fernandez-Bolanos J.G., Fuentes J., Robina I. Tetrahedron Lett. 42:2001;1283-1285
28. Robina I., Moreno-Vargas A.J., Fernandez-Bolanos J.G., Fuentes J., Demange R., Vogel P. Bioorg. Med. Chem. Lett. 11:2001;2555-2559
29. Moreno-Vargas A.J., Robina I., Demange R., Vogel P. Helv. Chim. Acta. 86:2003;1894-1913
30. Garcia Gonzalez F. Adv. Carbohydr. Chem. 11:1956;97-143
31. Garcia Ganzalez F., Gomez Sanchez A. Adv. Carbohydr. Chem. 20:1965;303-355
32. Gomez Sanchez A., Rodriguez Roldan A. Carbohydr. Res. 22:1972;53-62
33. Kozikowski A.P., Lin G.Q., Springer J.P. Tetrahedron Lett. 28:1987;2211-2214
34. Rodrigues F., Canac Y., Lubineau A. Chem. Commun. (Cambridge). 2000;2049-2050
35. Imamoto T. Lanthanides in Organic Chemistry. 1994;Academic, New York
36. Satheesh Babu R. Synlett. 2002;1935-1936
37. Deo M.D., Marcantoni E., Torregiani E.J. Org. Chem. 65:2000;2830-2833
38. Sabitha G., Satheesh Babu R., Rajkumar M., Jadav J.S. Org. Lett. 4:2002;343-345
39. Bartoli G., Bosco M., Bellucci M.C., Marcantoni E., Sambri L., Torregiani E. Eur. J. Org. Chem. 1999;617-620
40. Yadav J.S., Reddy B.V.S. Synlett. 2000;1275-1276
41. Fukuzawa S., Fukushima M., Fujinama T., Sakai S. Bull. Chem. Soc. Jpn. 62:1989;2348-2352
42. Kobayashi S. Synlett. 1994;689-701. and references cited therein
43. Loh T.P., Tan K.T., Hu Q.-Y. Angew. Chem., Int. Ed. 40:2001;2921-2922
44. Muthuswami S., Babu S.A., Gunanathan C. Tetrahedron Lett. 43:2002;3133-3136
45. Frost C.G., Haitley J.P., Griffin D. Synlett. 2002;1928-1930
46. Yu L.-B., Chen D., Li J., Ramirez J., Wang P.G. J. Org. Chem. 62:1997;903-907
47. Xie W., Bloomfield K.M., Jin Y., Dolney N.Y., Wang P.G. Synlett. 1999;498-500
48. Akiyama T., Iwai J. Tetrahedron Lett. 38:1997;853-856