Regioselective synthesis of 6-S-alkyl and 6-S-glycosyl-6-thio-d-mannofuranose derivatives from 5,6-O-cyclic sulfate precursors

Carbohydrate Research

Volumn 342, Issue 11, 2007, Pages 1490-1495

  Wadouachi, Anne ^a   Lescureux, Ludivine ^a   Lesur, David ^a   Beaupère, Daniel ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

6 S Alkyl 6 thio d mannofuranose; Cyclic sulfates; Cyclic sulfite; Nucleophilic opening; S Alkyl thiomannofuranose; Thiodisaccharides

Indexed keywords

MANNOFURANOSE; REACTION TIMES; THIOLATE ANION;

HYDROLYSIS; NEGATIVE IONS; ORGANIC COMPOUNDS; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

SUGARS;

2,3 O ISOPROPYLIDENE 6 S (1,2:3,4 DI O ISOPROPYLIDENE ALPHA DEXTRO GALACTOPYRANOS 6 YL) 6 THIO ALPHA DEXTRO MANNOFURANOSE; 2,3 O ISOPROPYLIDENE 6 S (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 6 THIO ALPHA DEXTRO MANNOFURANOSIDE; 5,6 O CYCLIC SULFATE; 6 S ALKYL 6 THIO DEXTRO MANNOFURANOSE; 6 S GLYCOSYL 6 THIO DEXTRO MANNOFURANOSE; CARBOHYDRATE DERIVATIVE; METHYL 2,3 O ISOPROPYLIDENE 6 S (2,3,4,6 TETRA O ACETYL NETA DEXTRO GLUCOPYRANOSYL) 6 THIO ALPHA DEXTRO MANNOFURANOSIDE; SUGAR; SULFATE; UNCLASSIFIED DRUG;

ARTICLE; HYDROLYSIS; PRIORITY JOURNAL; SYNTHESIS;

CYCLIC S-OXIDES; MAGNETIC RESONANCE SPECTROSCOPY; MANNOSE; MANNOSIDES; MONOSACCHARIDES; SULFATES;

TETRA;

EID: 34250672785     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2007.05.016     Document Type: Article

References (30)

1. El Ashry E.S.H., Rashed N., and Shobier A.H. Die Pharmazie 55 (2000) 251-262
2. Dey P.M., and Witczak Z.J. Mini-Rev. Med. Chem. 3 (2003) 271-280
3. Witczak Z.J., and Culhane J.M. Appl. Microbiol. Biotechnol. 69 (2005) 237-244
4. Szilagyi L., and Varela O. Curr. Org. Chem. 10 (2006) 1745-1770
5. Greimel P., Spreitz J., Stütz A.E., and Wrodnigg T. Org. Chem. Sugars (2006) 383-424
6. Lalot J., Manier G., Stasik I., Demailly G., and Beaupère D. Carbohydr. Res. 335 (2001) 55-61
7. Lalot J., Stasik I., Beaupère D., and Godé P. J. Therm. Anal. Calorim. 74 (2003) 77-83
8. Lalot J., Stasik I., Beaupère D., and Godé P. J. Colloid Interface Sci. 273 (2004) 604-610
9. Chaveriat L., Stasik I., Demailly G., and Beaupère D. Carbohydr. Res. 339 (2004) 1817-1821
10. Driguez H. Chem Bio Chem 2 (2001) 311-318
11. Jahn M., Warren R.A.J., and Withers S.G. Angew. Chem., Int. Ed. 42 (2003) 352-354
12. Bundle D.R., Rich J.R., Jacques S., Yu H.N., Nitz M., and Ling C.C. Angew. Chem., Int. Ed. 44 (2005) 7725-7729
13. Morais L.L., Yuasa H.B., Bennis K., Ripoche I., and Auzanneau F.I. Can. J. Chem. 84 (2006) 587-596
14. Hellmuth H., Hillringhaus L., Hoebbel S., Kraj S., Dijkuizen L., and Seibel J. ChemBioChem 8 (2007) 273-276
15. Comber R.N., Friedrich J.D., Dunshee D.A., Petty S.L., and Secrist J.A. Carbohydr. Res. 262 (1994) 245-255
16. Hashimoto H., Shimada K., and Horito S. Tetrahedron: Asymmetry 5 (1994) 2351-2366
17. Witczak Z.J., Sun J., and Mielguj R. Bioorg. Med. Chem. Lett. 5 (1995) 2169-2174
18. Witczak Z.J., Kaplon P., and Markus Dey P. Carbohydr. Res. 338 (2003) 11-18
19. Uhrig M.L., Manzano V.E., and Varela O. Eur. J. Org. Chem. (2006) 162-168
20. For reviews see:. Lohray B.B. Synthesis (1992) 1035-1052
21. Bun H.S., He L., and Bittman R. Tetrahedron 56 (2000) 7051-7091
22. Gourlain T., Wadouachi A., and Beaupere D. Carbohydr. Lett. 2 (1996) 143-148
23. Gourlain T., Wadouachi A., Uzan R., and Beaupere D. J. Carbohydr. Chem. 16 (1997) 1089-1100
24. Gourlain T., Wadouachi A., and Beaupere D. Synthesis 2 (1999) 290-294
25. Gourlain T., Wadouachi A., and Beaupere D. Carbohydr. Res. 324 (2000) 66-73
26. Van der Klein P.A.M., and van Boom J.H. Carbohydr. Res. 224 (1992) 193-200
27. Wadouachi A., Beaupère D., Uzan R., Stasik I., Ewing D.F., and Mackenzie G. Carbohydr. Res. 262 (1994) 147-154
28. Kim B.M., and Sharpless K.B. Tetrahedron Lett. 30 6 (1989) 655-658
29. Calvo-Asin J.A., Calvo-Flores F.G., Exposito-Lopez J.M., Hernandez-Mateo F., Garcia-Lopez J.J., Isac-Garcia J., Santoyo-Gonzalez F., and Vargas-Berenguel A. J. Chem. Soc., Perkin Trans. 1 (1997) 1079-1081
30. Alho M.A.M., D'Accorso N.B., and Thiel I.M.E. J. Heterocycl. Chem. 33 (1996) 1339-1343