Formation of β-lactams fused to the pyranoid ring via the Mitsunobu reaction

Carbohydrate Research

Volumn 307, Issue 1-2, 1998, Pages 33-43

  Zegrocka, O ^a   Abramski, W ^a   Urbanczyk Lipkowska Z ^a   Chmielewski, M ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Lactams; 2 C:3 N Carbonyl 2,3 dideoxy 3 N tosylamino L lyxo and D ribopyranosides; Intramolecular Mitsunobu reaction; N Tosyl 2 C carbamoyl glycosides

Indexed keywords

BETA LACTAM DERIVATIVE;

ALKYLATION; ARTICLE; GLYCOSYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032004105     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00017-2     Document Type: Article

References (27)

1. [1] D.J. Hart and D.-Ch. Ha, Tetrahedron Lett., 26 (1985) 5493-5496; J. Gallucci, D.-Ch. Ha, and D.J. Hart, Tetrahedron, 45 (1989) 1283-1292.
2. [1] D.J. Hart and D.-Ch. Ha, Tetrahedron Lett., 26 (1985) 5493-5496; J. Gallucci, D.-Ch. Ha, and D.J. Hart, Tetrahedron, 45 (1989) 1283-1292.
3. [2] A. Knierzinger and A. Vasella, J. Chem. Soc., Chem. Commun., (1984) 9-11.
4. [3] M. Chmielewski and J. Grodner, J. Carbohydr. Chem., 11 (1992)691-698.
5. [4] C. Bełzecki and M. Chmielewski, J. Carbohydr. Chem., 13 (1994) 1103-1114; J. Grodner and M. Chmielewski, Tetrahedron, 51 (1995) 829-836.
6. [4] C. Bełzecki and M. Chmielewski, J. Carbohydr. Chem., 13 (1994) 1103-1114; J. Grodner and M. Chmielewski, Tetrahedron, 51 (1995) 829-836.
7. [5] D. Mostowicz and M. Chmielewski, Carbohydr. Lett., 1 (1994) 95-98.
8. [6] M. Chmielewski, Z. Kałuza, J. Grodner, and R. Urbański, in R.M. Guliano (Ed.), Cycloaddition Reactions in Carbohydrate Chemistry, ACS Symposium Series, 494 (1992) 50-65.
9. [7] M. Chmielewski, Z. Kałuza, and B. Furman, J. Chem. Soc., Chem. Commun., (1996) 2689-2696.
10. [8] R.H. Hall, A. Jordaan, and G.J. Laurens, J. Chem. Soc., (1973) 38-44; R.H. Hall, A. Jordaan, and O.G. de Villiers, J. Chem. Soc., (1975) 626-629.
11. [8] R.H. Hall, A. Jordaan, and G.J. Laurens, J. Chem. Soc., (1973) 38-44; R.H. Hall, A. Jordaan, and O.G. de Villiers, J. Chem. Soc., (1975) 626-629.
12. [9] D. Mostowicz, C. Bełzecki, and M. Chmielewski, J. Carbohydr. Chem., 7 (1988) 805-810.
13. [10] D. Mostowicz, O. Zegrocka, and M. Chmielewski, Carbohydr. Res., 212 (1991) 283-288.
14. [11] A.M. Pantard and S.A. Evans, J. Org. Chem., 53 (1988) 2300-2303.
15. [12] O. Mitsunobu, J. Kimura, K. Izumi, and N. Yamagida, Bull. Chem. Soc. Jpn., 49 (1976) 510-513.
16. [13] H.H. Brandstetter and E. Zbiral, Helv. Chim. Acta, 63 (1980) 327-343; R.D. Guthrie, I.D. Jenkins, R. Yamasaki, B.W. Skeleton, and A.H. White, J. Chem. Soc., Perkin Trans. 1, (1981) 2328-2334; R.J. Ferrier, P. Schmidt, and P.C. Tyler, J. Chem. Soc., Perkin Trans. 1, (1985) 301-303.
17. [13] H.H. Brandstetter and E. Zbiral, Helv. Chim. Acta, 63 (1980) 327-343; R.D. Guthrie, I.D. Jenkins, R. Yamasaki, B.W. Skeleton, and A.H. White, J. Chem. Soc., Perkin Trans. 1, (1981) 2328-2334; R.J. Ferrier, P. Schmidt, and P.C. Tyler, J. Chem. Soc., Perkin Trans. 1, (1985) 301-303.
18. [13] H.H. Brandstetter and E. Zbiral, Helv. Chim. Acta, 63 (1980) 327-343; R.D. Guthrie, I.D. Jenkins, R. Yamasaki, B.W. Skeleton, and A.H. White, J. Chem. Soc., Perkin Trans. 1, (1981) 2328-2334; R.J. Ferrier, P. Schmidt, and P.C. Tyler, J. Chem. Soc., Perkin Trans. 1, (1985) 301-303.
19. [14] N. Nakata, Tetrahedron, 19 (1963) 1959-1963; P.E. Morris Jr., D.E. Kiely, G.S. Vigee, and P. Kóvàč, J. Carbohydr. Chem., 9 (1990) 661-673.
20. [14] N. Nakata, Tetrahedron, 19 (1963) 1959-1963; P.E. Morris Jr., D.E. Kiely, G.S. Vigee, and P. Kóvàč, J. Carbohydr. Chem., 9 (1990) 661-673.
21. [15] M. Chmielewski, Z. Kałuza, H. Dodziuk, K. Suwińska, D. Rosenbaum, H. Duddeck, P. Magnus, and J.C. Huffman, Carbohydr. Res., 203 (1990) 183-194.
22. [16] Z. Urbańczyk-Lipkowska, K. Suwińska, R. Luboradzki, D. Mostowicz, Z. Kałuza, J. Grodner, and M. Chmielewski, Carbohydr. Res., 256 (1994) 1-11.
23. [17] Z. Urbańczyk-Lipkowska, K. Suwińska, D. Mostowicz, and M. Chmielewski, J. Chem. Cryst., 25 (1995) 693-699.
24. [18] J.E. Baldwin, A.J. Edwards, Ch.N. Farthing, and A.T. Russell, Synlett, (1993) 49-50 and references cited therein.
25. [19] J.E. Baldwin, R.M. Adlington, Ch.R.A. Godfrey, D.W. Gollins, M.L. Smith, and A.T. Russell, Synlett, (1993) 51-53.
26. [20] G.M. Sheldrick, Acta Cryst., A 46 (1990) 467.
27. [21] G.M. Sheldrick, Shelxl 93. Program for Refinement of Crystal Structure. University of Göttingen, 1993.