An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-d-glucamine

Tetrahedron

Volumn 64, Issue 27, 2008, Pages 6377-6386

  Martínez, R Fernando ^a   Ávalos, Martín ^a   Babiano, Reyes ^a   Cintas, Pedro ^a   Jiménez, José L ^a   Light, Mark E ^b   Palacios, Juan C ^a   Pérez, Esther M S ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; C NUCLEOSIDE; MEGLUMINE; OXAZOLIDINE DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL REACTION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 44349180204     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.082     Document Type: Article

References (39)

1. Kool E.T. Acc. Chem. Res. 35 (2002) 936
2. Ramesh N.G., and Balasubramanian K.K. Eur. J. Org. Chem. (2003) 4477
3. Henry A.A., and Romesberg F.E. Curr. Opin. Chem. Biol. 7 (2003) 727
4. Nasr A.Z. Nucleosides Nucleotides Nucleic Acids 23 (2004) 1825
5. Wellington K.W., and Benner S.A. Nucleosides Nucleotides Nucleic Acids 25 (2006) 1309
6. Alonso-Cruz C.R., Freire R., Rodríguez M.S., and Suárez E. Synlett (2007) 2723
7. Avalos M., Babiano R., Cintas P., Jiménez J.L., Light M.E., Palacios J.C., and Pérez E.M.S. J. Org. Chem. 73 (2008) 661
8. Steif F., Wibbeling B., Meyer O., and Hoppe D. Synthesis (2000) 743
9. Vega-Pérez J.M., Vega M., Blanco E., and Iglesias-Guerra F. Tetrahedron: Asymmetry 12 (2001) 3189
10. Shen M., and Li C. J. Org. Chem. 69 (2004) 7906
11. Spino C., Tremblay M.-C., and Gobdout C. Org. Lett. 6 (2004) 2801
12. Elzner S., Maas S., Engel S., and Kunz H. Synthesis (2004) 2153
13. Gessier F., Schaeffer L., Kimmerlin T., Flögel O., and Seebach D. Helv. Chim. Acta 88 (2005) 2235
14. Hein J.E., Geary L.M., Jaworski A.A., and Hultin P.G. J. Org. Chem. 70 (2005) 9940
15. Gnas Y., and Glorius F. Synthesis (2006) 1899
16. Bruschi M., Orlandi M., Rindone B., Rummakko P., and Zoia L. J. Phys. Org. Chem. 19 (2006) 592
17. Chavda S., Coumbarides G.S., Dingjan M., Eames J., Flinn A., and Northen J. Chirality 19 (2007) 313
18. For a revision on the cyclization of iminium ions en route to chiral heterocycles, see:. Royer J., Bonin M., and Micouin L. Chem. Rev. 104 (2004) 2311
19. Ide W.S., and Buck J.S. Org. React. 4 (1948) 269
20. Neuvonen K., Fülöp F., Neuvonen H., Koch A., Kleinpeter E., and Pihlaja K. J. Org. Chem. 66 (2001) 4132
21. Fülöp F., and Pihlaja K. Tetrahedron 49 (1993) 6701
22. Fülöp F., Pihlaja K., Neuvonen K., Bernáth G., Argay G., and Kálmán A. J. Org. Chem. 58 (1993) 1967
23. Maireanu C., Darabantu M., Plé G., Berghian C., Condamine E., Ramondenc Y., Silaghi-Dumitrescu I., and Mager S. Tetrahedron 58 (2002) 2681
24. Bock K., and Pedersen C. Adv. Carbohydr. Chem. Biochem. 41 (1983) 27
25. Avalos M., Babiano R., Cintas P., Hursthouse M.B., Jiménez J.L., Light M.E., Palacios J.C., and Pérez E.M.S. Eur. J. Org. Chem. (2006) 657
26. -3, θ range (3.03-27.48°). Crystal data for compound 19 have been deposited with the Cambridge Crystallographic Data Centre (CCDC-665884) and can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
27. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734
28. Smith M.B., and March J. Advanced Organic Chemistry. 5th ed. (2001), Wiley, New York, NY Chapter 6, pp 282-284
29. Alva M.E., Chokotho N.C.J., Jarvis T.C., David C., Lewis C.C., and McDonnell P.D. Tetrahedron 41 (1985) 5919
30. Just G., Potvin P., and Uggowitzer P. J. Org. Chem. 48 (1983) 2923
31. Khruscheva N.S., Loim N.M., Sokolov V.I., and Makhaev V.D. J. Chem. Soc., Perkin Trans. 1 (1997) 2425
32. Stoddart J.F. Stereochemistry of Carbohydrates (1971), Wiley, New York, NY Chapter 3, pp 55-58
33. Becke A.D. J. Chem. Phys. 98 (1993) 5648
34. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 75
35. Cancès M.T., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
36. Cossi M., Barone V., Mennucci B., and Tomasi J. Chem. Phys. Lett. 286 (1998) 253
37. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151
38. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
39. Horton D., and Wander J.D. J. Org. Chem. 39 (1974) 1859