One-pot multicomponent synthesis of 2,3-dihydropyrans: new access to furanose-pyranose 1,3-C-C-linked-disaccharides

Tetrahedron Letters

Volumn 50, Issue 14, 2009, Pages 1526-1528

  Castagnolo, Daniele ^a   Botta, Lorenzo ^a   Botta, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

Dihydropyrans; Disaccharide; Enyne metathesis; Hetero Diels Alder; Multicomponent reaction

Indexed keywords

2 PYRONE DERIVATIVE; DISACCHARIDE; FURAN; PYRAN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESILYLATION; DIASTEREOISOMER; DIELS ALDER REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROWAVE IRRADIATION; OLEFINATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ALNUS;

EID: 60249097957     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.047     Document Type: Article

References (30)

1. Strecker A. Justus Liebigs Ann. Chem. 75 (1850) 27-45
2. For recent reviews of multicomponent reactions, see:. Ramon D.J., and Yus M. Angew. Chem., Int. Ed. 44 (2005) 1602-1634
3. Tietze L.F. Chem. Rev. 96 (1996) 115-136
4. Tietze L.F., and Beifus U. Angew. Chem., Int. Ed. 32 (1993) 131-163
5. Strubing D., Neumann H., Hubner S., Klaus S., and Beller M. Tetrahedron 61 (2005) 11345-11354
6. Nair V., Sreekumar V., Bindu S., and Suresh E. Org. Lett. 7 (2005) 2297-2300
7. Oishi T., and Ohtsuka Y. In: Atta-ur-Rahman (Ed). Studies in Natural Products Synthesis Vol. 3 (1989), Elsevier, Amsterdam 73
8. Yet L. Chem. Rev. 100 (2000) 2963-3007
9. Boivin T.L.B. Tetrahedron 43 (1987) 3309-3362
10. Coppi L., Ricci A., and Taddei M. J. Org. Chem. 53 (1988) 911-913
11. Li C.-J., and Zhang W.-C. Tetrahedron 56 (2000) 2403-2411
12. Schmidt B., and Westhus M. Tetrahedron 56 (2000) 2421-2426
13. Nicolaou K.C., and Sorensen E.J. Classics in Total Synthesis (1996), VCH, Weinheim
14. Class Y.J., and DeShong P. Chem. Rev. 95 (1995) 1843-1857
15. Castagnolo D., Renzulli M.L., Galletti E., Corelli F., and Botta M. Tetrahedron: Asymmetry 16 (2005) 2893-2896
16. Castagnolo D., Giorgi G., Spinosa R., Corelli F., and Botta M. Eur. J. Org. Chem. (2007) 3676-3686
17. For recent general reviews on C-glycosides see:. Liu L., McKee M., and Postema M.H.D. Curr. Org. Chem. 5 (2001) 1133-1167
18. Dondoni A. Pure Appl. Chem. 72 (2000) 1577-1588
19. Dondoni A., and Marra A. Chem. Rev. 100 (2000) 4395-4421
20. Bertozzi C., and Bednarski M. Synthesis of C-Glycosides; Stable Mimics of O-Glycosidic Linkages. Frontiers in Natural Product Research (Modern Methods in Carbohydrate Synthesis) Vol. 1 (1996), Harwood Academic 316-351
21. Armstrong R.W., and Teegarden B.R. J. Org. Chem. 57 (1992) 915-922
22. Guerrini M., Guglieri S., Santarsiero R., and Vismara E. Tetrahedron: Asymmetry 16 (2005) 243-253
23. Giessert A.J., Snyder L., Markham J., and Diver S.T. Org. Lett. 5 (2003) 1793-1796
24. Bataille C., Begin G., Guillam A., Lemiegre L., Lys C., Maddaluno J., and Toupet L. J. Org. Chem. 67 (2002) 8054-8062
25. Beccalli E.M., Marchesini A., and Pilati T. Tetrahedron 52 (1996) 3029-3036
26. 9a,b but using butylvinylether as dienophile, led to endo adduct as the major product.
27. 2O/hexanes as the eluent to yield the 2,3-dihydropyrans 5a-h (as a 1:2 mixture of cis/trans-isomers) as tan oils.
28. Haraguchi K., Sumino M., and Tanaka H. J. Org. Chem. 71 (2006) 4433-4438
29. Determined by chiral HPLC-MS using an (S,S)-Whelk-O1 column (methanol/water 70:30, flow rate 0.8 mL/min, UV-254 nm).
30. 11: C, 67.07; H, 5.63. Found. C, 67.32; H, 5.89.