PhBCl2 promoted reductive opening of 2′,4′-O-p- methoxybenzylidene: New regioselective differentiation of position 2′ and 4′ of α-L-iduronyl moieties in disaccharide building blocks

Tetrahedron Letters

Volumn 45, Issue 18, 2004, Pages 3643-3645

  Dilhas, Anna ^a   Bonnaffé, David ^a  

^a CNRS   (France)

Author keywords

Combinatorial chemistry; Glycosylation; Heparan sulfate; Heparin; Oligosaccharides; Reductive acetal opening

Indexed keywords

ACETAL DERIVATIVE; BENZYLIDENE DERIVATIVE; CHLORINE DERIVATIVE; DISACCHARIDE; IDURONIC ACID; REAGENT;

ARTICLE; METHODOLOGY; PROTECTION; REDUCTION;

EID: 1842787077     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.046     Document Type: Article

References (20)

1. Capila I., Linhardt R.J. Angew. Chem., Int. Ed. 41:2002;390-412.
2. Lortat Jacob H., Grosdidier A., Imberty A. Proc. Natl. Acad. Sci. U.S.A. 99:2002;1229-1234.
3. Esko J.D., Lindhal U. J. Clin. Invest. 108:2001;169-173.
4. Lindhal U., Kusche-Gullberg M., Kjellen L. J. Biol. Chem. 273:1998;24979-24982.
5. Gallagher J.T. Biochem. Soc. Trans. 25:1997;1206-1209.
6. Gavard O., Hersant Y., Alais J., Duverger V., Dilhas A., Bascou A., Bonnaffé D. Eur. J. Org. Chem. 2003;3603-3620.
7. Van Boeckel C.A.A., Petitou M. Angew. Chem., Int. Ed. 32:1993;1671-1818.
8. Tabeur C., Machetto F., Malet J.-M., Duchaussoy P., Petitou M., Sinaÿ P. Carbohydr. Res. 281:1996;253-276.
9. Barroca N., Jacquinet J.C. Carbohydr. Res. 337:2002;673-689.
10. Poletti L., Lay L. Eur. J. Org. Chem. 2003;2999-3024.
11. Karst N.A., Linhardt R.J. Curr. Med. Chem. 10:2003;1993-2031.
12. Prabhu A., Venot A., Boons G.-J. Org. Lett. 5:2003;4975-4978.
13. Lohman G.J.S., Hunt D.K., Högermeier J.A., Seeberger P.H. J. Org. Chem. 68:2003;7559-7561.
14. de Paz J.-L., Ojeda R., Reichardt N., Martin-Lomas M. Eur. J. Org. Chem. 2003;3308-3324.
15. Sakagami M., Hamana H. Tetrahedron Lett. 41:2000;5547-5551.
16. Ratner D.M., Swansson E.R., Seeberger P.E. Org. Lett. 5:2003;4717-4720.
17. Jacquinet J.C., Petitou M., Duchaussoy P., Lederman I., Choay J., Torri G., Sinaÿ P. Carbohydr. Res. 130:1984;221-241.
18. Lubineau A., Gavard O., Alais J., Bonnaffé D. Tetrahedron Lett. 41:2000;307-311.
19. Dilhas A., Bonnaffé D. Carbohydr. Res. 338:2003;681-686.
20. Lamberth C., Bednarski M.D. Tetrahedron Lett. 32:1991;7369-7372.