Alternative approaches towards glycosylated eight-membered ring compounds employing Claisen rearrangement of mono and disaccharide allyl vinyl ether precursors

Tetrahedron Asymmetry

Volumn 16, Issue 9, 2005, Pages 1631-1638

  Jürs, Stefan ^a   Thiem, Joachim ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; ETHER DERIVATIVE; GLYCOSIDE; MONOSACCHARIDE;

ARTICLE; CHEMICAL REACTION KINETICS; CLAISEN REARRANGEMENT; GLYCOSYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 17844392842     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.02.027     Document Type: Article

References (20)

1. Q.-W. Shi, F. Sauriol, O. Mamer, and L.O. Zamir J. Nat. Prod. 66 2003 1480 1485
2. T. Sassa, N. Tajima, M. Sato, A. Takahashi, and N. Kato Biosci. Biotechnol. Biochem. 66 2002 2356 2361
3. N. Tajima, M. Nukina, N. Kato, and T. Sassa Biosci. Biotechnol. Biochem. 68 2004 1125 1130
4. E. Marre, R. Colombo, P. Lado, and F. Rasi-Caldogno Plant Sci. Lett. 2 1974 139 150
5. A. Ballio, M.I. De Michelis, P. Lado, and G. Randazzo Physiol. Plant. 52 1981 471 475
6. B. Werschkun, and J. Thiem Angew. Chem. 109 1997 2905 2906
7. Angew. Chem., Int. Ed. 36 1997 2793 2794
8. W. Wang, Y. Zhang, M. Sollogoub, and P. Sinaÿ Angew. Chem. 112 2000 2588 2590
9. Angew. Chem., Int. Ed. 39 2000 2466 2467
10. In analogy to: M.L. Shulman, S.D. Shiyan, and A.Y. Khorlin Carbohydr. Res. 33 1974 229 235
11. D. Horton, and W. Weckerle Carbohydr. Res. 44 1975 227 240
12. N.A. Petasis, and M.A. Patane Tetrahedron 48 1992 5757 5821
13. The glycosylation step was performed employing the 'Inverse Procedure', viz adding the dissolved donor to the mixture of acceptor and promotor (15 mol %) at 0°C under argon: R.R. Schmidt, and A. Toepfer Tetrahedron Lett. 32 1991 3353 3356
14. R.R. Schmidt, J. Michel, and M. Roos Liebigs Ann. Chem. 22 1984 1343 1357
15. Large amounts of AgF were required to effect complete elimination leading in turn to significant losses of product during workup due to adsorption on silver salts
16. L.A. Paquette, D. Friedrich, and R.D. Rogers J. Org. Chem. 56 1991 3841 3849
17. P.A.V. van Hooft, G.A. van der Marel, C.A.A. van Boeckel, and J.H. van Boom Tetrahedron Lett. 42 2001 1769 1772
18. Nomenclature of Carbohydrates (Recommendations 1996), Carbohydr. Res. 1997, 297, 1-92
19. R.U. Lemieux Methods Carbohydr. Chem. 32 1963 221 222
20. P.A. Levene, and R.S. Tipson J. Biol. Chem. 90 1931 89 98