Remarkable high-pressure enhancement of enantiopure nitrone cycloadditions to glycals: General access to (1→2)-linked pseudo aza-C-disaccharides

Synlett

Volumn , Issue 12, 1998, Pages 1444-1446

  Cardona, Francesca ^a   Salanski, Piotr ^b   Chmielewski, Marek ^b   Valenza, Silvia ^a   Goti, Andrea ^a   Brandi, Alberto ^a  

^a CNR   (Italy)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001901016     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1940     Document Type: Article

References (27)

1. Some recent examples of syntheses of aza-C-disaccharides: Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991.
2. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252.
3. Kraehenbuehl, K.; Picasso, S.; Vogel, P. Bioorg. & Med. Chem. Lett. 1997, 7, 893.
4. Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856.
5. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
6. Dong, W.; Jespersen, T.; Bols, M.; Skrydstrup, T.; Sierks, M. R. Biochemistry 1996, 35, 2788.
7. (a) Cardona, F.; Valenza, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1997, 38, 8097.
8. (b) Cardona, F.; Valenza, S.; Picasso S.; Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311.
9. For reviews about synthesis under high pressure see: Matsumoto, K.; Acheson, R. M. Organic Synthesis at High Pressures; John Wiley & Sons: NewYork, 1991.
10. Jurczak, J., Baranowski, B. Eds. High Pressure Synthesis; Elsevier: Amsterdam, 1989.
11. Isaacs, N. S. Tetrahedron 1991, 47, 8463.
12. van Eldik, R.; Asano, T.; le Noble, W. Chem. Rev. 1989, 89, 549.
13. Yoshimura, Y.; Osugi, J.; Nakahara, M. J. Am. Chem. Soc. 1983, 105, 5414.
14. For [2+2] and [4+2] cycloadditions to glycals under high pressure see: Chmielewski, M.; Kaluza, Z.; Belzecki, C.; Salanski, P.; Jurczak, J.; Adamowicz, H. Tetrahedron 1985, 41, 2441.
15. Chmielewski, M.; Kaluza, Z.; Mostowicz, D.; Belzecki, C.; Baranowska, E.; Jacobsen, J. P.; Salanski, P.; Jurczak, J. Tetrahedron 1987, 43, 4555.
16. Only few studies of nitrone cycloadditions under high pressure have been reported. See for example: (a) Dicken, C. M.; DeShong, P. J. Org. Chem. 1982, 47, 2047.
17. (b) Padwa, A.; Kline, D. N.; Norman, B. H. J. Org. Chem. 1989, 54, 810.
18. (c) Katagiri, N.; Watanabe, N.; Sakaki, J.-i.; Kawai, T.; Kaneko, C. Tetrahedron Lett. 1990, 32, 4633.
19. (d) Seerden, J.-P. G.; Boeren, M. M. M.; Scheeren, H. W. Tetrahedron 1997, 53, 11843.
20. 7d
21. Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274.
22. Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743.
23. General procedures for high pressure cycloadditions: Reactions of nitrones 5-9 with glycals 10-15 were carried out at 60°C in toluene for 68 h. The reaction mixture (0.17 mmol of nitrone, 0.34 mmol of glycal and 0.5 mL of toluene) was placed in a Teflon ampoule which was inserted into the high-pressure vessel filled with hexane as a transmission medium. After decompression, the mixture was purified by flash column chromatography.
24. No improvement was observed with a more polar solvent such as acetonitrile. More dilute solutions afforded lower yields.
25. 3) δ 170.2 (s, 1C), 166.0 (s, 1C), 99.7 (d, 1C), 77.3 (d, 1C), 76.9 (d, 1C), 74.5 (s, 1C), 73.7 (s, 1C), 73.6 (d, 1C), 72.5 (d, 1C), 69.1 (d, 1C), 66.9 (d, 1C), 60.5 (t, 1C), 47.4 (d, 1C), 28.9 (q, 1C), 28.4 (q, 3C), 28.3 (q, 3C), 20.7 (q, 1C), 17.4 (q, 1C).
26. A similar lower reactivity of these galactals was also observed in the atmospheric pressure reactions.
27. Two of these adducts, after deprotection, showed selective inhibition towards amyloglucosidase.