Alkylalanes and methyl furanosides: regioselective O-debenzylation or acetal cleavage

Carbohydrate Research

Volumn 341, Issue 12, 2006, Pages 2135-2144

  Jia, Cai ^a,b,c   Zhang, Yongmin ^a,b   Zhang, Li He ^c   Sinaÿ, Pierre ^a,b   Sollogoub, Matthieu ^a,b  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b SORBONNE UNIVERSITÉ   (France)

^c PEKING UNIVERSITY   (China)

Author keywords

Acetal cleavage; Aluminium; Furanose; Regioselective deprotection

Indexed keywords

ALUMINUM; DERIVATIVES; REACTION KINETICS;

ACETAL CLEAVAGE; FURANOSE; REGIOSELECTIVE DEPROTECTION;

ORGANIC COMPOUNDS;

ACETAL DERIVATIVE; ALKYL GROUP; ALUMINUM; FURAN DERIVATIVE; PENTOSE; REAGENT;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEBENZYLATION; DEPROTECTION REACTION; METHYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ACETALS; BENZYL COMPOUNDS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; MAGNETIC RESONANCE SPECTROSCOPY; METHYLGLYCOSIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33745712334     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.05.002     Document Type: Article

References (19)

1. For example see:. Weissman S.A., and Zewge D. Tetrahedron 61 (2005) 7833-7863
2. Sollogoub M., Das S.K., Mallet J.-M., and Sinaÿ P. C. R. Acad. Sci. Paris, t.2, Série IIc (1999) 441-448
3. Lecourt T., Hérault A., Pearce A.J., Sollogoub M., and Sinaÿ P. Chem. Eur. J. 12 (2004) 2960-2971
4. Meng X., Zhang Y., Sollogoub M., and Sinaÿ P. Tetrahedron Lett. 45 (2004) 8165-8168
5. Bistri O., Sinaÿ P., and Sollogoub M. Tetrahedron Lett. 46 (2005) 7757-7760
6. Bistri O., Sinaÿ P., and Sollogoub M. Chem. Commun. (2006) 1112-1114
7. Jia C., Pearce A.J., Blériot Y., Zhang Y., Zhang L.-H., Sollogoub M., and Sinaÿ P. Tetrahedron: Asymmetry 15 (2004) 699-703
8. Kawana M., Kuzuhara H., and Emoto S. Bull. Chem. Soc. Jpn. 54 (1981) 1492-1504
9. Su T.-L., Klein R.S., and Fox J.J. J. Org. Chem. 47 (1982) 1506-1509
10. Ning J., and Kong F. Carbohydr. Res. 300 (1997) 355-360
11. Hirooka M., Mori Y., Sasaki A., Koto S., Shinoda Y., and Morinaga A. Bull. Chem. Soc. Jpn. 74 (2001) 1679-1694
12. Selected examples:. Kawana M. Chem. Lett. (1981) 1541-1542
13. Hori H., Nishida Y., Ohrui H., and Meguro H. J. Org. Chem. 54 (1989) 1346-1353
14. Martin P. Helv. Chim. Acta 78 (1995) 486-504
15. Bouzide A., and Sauvé G. Tetrahedron Lett. 40 (1999) 2883-2886
16. Falck J.R., Barma D.K., Venkataraman S.K., Baati R., and Mioskowski C. Tetrahedron Lett. 43 (2002) 963-966
17. Martin O.R., Rao S.P., Yang T.-F., and Fotia F. Synlett (1991) 702-704
18. Hirota K., Mongushi Y., Kitade Y., and Sajiki H. Tetrahedron 53 (1997) 16683-16698
19. Olsson R., Rundström P., and Frejd T. J. Chem. Soc., Perkin Trans. 1 (1998) 785-790