Dramatic effect of PSE clamping on the behaviour of d-glucal under Ferrier I conditions

Tetrahedron Letters

Volumn 49, Issue 21, 2008, Pages 3484-3488

  Fernandes, Anthony ^a   Dell'Olmo, Maxime ^a   Tatibouët, Arnaud ^a   Imberty, Anne ^b   Philouze, Christian ^c   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^c Université Grenoble I   (France)

Author keywords

Ferrier I reaction; Glycals; Glycosylation; Phenylsulfonylethylidene (PSE) acetals

Indexed keywords

ACETAL DERIVATIVE; GLUCONATE CALCIUM; LEWIS ACID; METHANOL; PHENYLSULFONYLETHYLIDENE;

ACYLATION; ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 43049156402     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.093     Document Type: Article

References (24)

1. Haines A.H. Adv. Carbohydr. Chem. Biochem. 39 (1981) 13-70
2. Gelas J. Adv. Carbohydr. Chem. Biochem. 39 (1981) 71-156
3. Chéry F., Rollin P., De Lucchi O., and Cossu S. Tetrahedron Lett. 41 (2000) 2357-2360
4. Chéry F., Rollin P., De Lucchi O., and Cossu S. Synthesis (2001) 286-292
5. Cabianca E., Tatibouët A., and Rollin P. Pol. J. Chem. 79 (2005) 317-322
6. Chevalier-du Roizel B., Cabianca E., Rollin P., and Sinaÿ P. Tetrahedron 58 (2002) 9579-9583
7. Ferrier R.J. Top. Curr. Chem. 215 (2001) 153-175
8. Procopio A., Dalpozzo R., De Nino A., Maiuolo L., Nardi M., Oliverio M., and Russo B. Carbohydr. Res. 342 (2007) 2125-2131
9. Rauter A.P., Almeida T., Xavier N.M., Siopa F., Vicente A.I., Lucas S.D., Marques J.P., Ribeiro F.R., Guisnet M., and Ferreira M.J. J. Mol. Catal., A: Chem. 275 (2007) 206-213
10. Kim H., Men H., and Lee C. J. Am. Chem. Soc. 126 (2004) 1336-1337
11. Hotha S., and Tripathi A. J. Comb. Chem. 7 (2005) 968-976
12. Marzabadi C.H., and Franck R.W. Tetrahedron 56 (2000) 8345-8417
13. Catelani G., Colonna F., and Rollin P. Gazz. Chim. Ital. 119 (1989) 389-393
14. Rauter A.P., Almeida T., Vicente A.I., Ribeiro V., Bordado J.C., Marques J.P., Ribeiro F.R., Ferreira M.J., Oliveira C., and Guisnet M. Eur. J. Org. Chem. (2006) 2429-2439
15. Sherry B.D., Loy R.N., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 4510-4511
16. Colinas P.A., and Bravo R.D. Org. Lett. 5 (2003) 4509-4511
17. Gopal Reddy B., Madhusudanan K.P., and Vankar Y.D. J. Org. Chem. 69 (2004) 2630-2633
18. Yadav J.S., Subba Reddy B.V., Vijaya Bhasker E., Raghavendra S., and Narsaiah A.V. Tetrahedron Lett. 48 (2007) 677-680
19. Seeberger P.H., Roehrig S., Schell P., Wang Y., and Christ W.J. Carbohydr. Res. 328 (2000) 61-69
20. Geiger J., Barroca N., and Schmidt R.R. Synlett (2004) 836-840
21. Strong bases readily induce ring opening of PSE acetals: Chéry, F.; Tatibouët, A.; De Lucchi, O.; Rollin, P., unpublished results.
22. 3)
23. 2).
24. CCDC 656182 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.