Glycosylidene carbenes: Part 31. Glycosylidene diaziridines: Stereoselective addition of ammonia and methylamine to lactone oxime sulfonates

Helvetica Chimica Acta

Volumn 86, Issue 5, 2003, Pages 1488-1521

  Bernet, Bruno ^a   Mangholz, Sissi E ^a   Briner, Karin ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; HYDROGEN BONDS; ISOMERS; STEREOCHEMISTRY;

STERIC INTERACTIONS;

ADDITION REACTIONS;

(2,3,5 TRI O BENZYL DEXTRO RIBOFURANOSYLIDENE)AMINOMETHANESULFONATE; 1,4 DIHYDRO 1,2,4,5 TETRAZINE; 2,3 DI O BENZYL DEXTRO MANNOPYRANOSYLIDENE DIAZIRIDINE; 2,3:5,6 DI O ISOPROPYLIDENE DEXTRO MANNOPYRANOSYLIDENE DIAZIRIDINE; AMMONIA; AZIRIDINE DERIVATIVE; CARBENOID; DEXTRO ARABINO 1,4 LACTONE OXIME METHANESULFONATE; GALACTO 1,5 LACTONE OXIME MESYLATE; GALACTOPYRANOSYLIDENE DIAZIRIDINE; GLYCOSYLIDENE DIAZIRIDINE; LACTONE DERIVATIVE; LACTONE OXIME SULFONATE; MANNOFURANOSYLIDENE DIAZIRIDINE; MANNONO 1,4 LACTONE OXIME SULFONATE; METHYLAMINE; NITROGEN 15; PENTONAMIDE; PENTONO 1,4 LACTONE; PYRANOSYLIDENE DIAZIRIDINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL BINDING; CONFORMATION; HYDROGEN BOND; ISOMERISM; ISOTOPE LABELING; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0038411322     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200390132     Document Type: Article

References (43)

1. C. Blüchel, A. Linden, A. Vasella, Helv. Chim. Acta 2001, 84, 3495.
2. A. Vasella, B. Bemet, M. Weber, W. Wenger, in 'Oligosaccharides in Chemistry and Biology; A Comprehensive Handbook', Ed. B. Ernst, John Wiley & Sons, New York, 2000, p. 156.
3. A. Vasella, in 'Bioorganic Chemistry: Carbohydrates', Ed. S. M. Hecht, Oxford University Press, New York, 1999, p. 56.
4. A. Vasella, Pure Appl. Chem. 1993, 65, 731.
5. A. Vasella, C. Witzig, C. Waldraff, P. Uhlmann, K. Briner, B. Bernet, L. Panza, R. Husi, Helv. Chim. Acta 1993, 76, 2847.
6. A. Vasella, Pure Appl. Chem. 1991, 63, 507.
7. K. Briner, A. Vasella, Helv. Chim. Acta 1989, 72, 1371.
8. M. Weber, A. Vasella, M. Textor, N. D. Spencer, Helv. Chim. Acta 1998, 81, 1359.
9. Semichem, 'AMPAC 6.0', 7128 Summit, Shawnee, KS 66216, 1998.
10. H. Spedding, J. Chem. Soc. 1961, 3617; H. Hönig, H. Weidmann, Carbohydr Res. 1979, 73, 260.
11. H. Spedding, J. Chem. Soc. 1961, 3617; H. Hönig, H. Weidmann, Carbohydr Res. 1979, 73, 260.
12. P. R. Muddasani, E. Bozo, B. Bemet, A. Vasella, Helv. Chim. Acta 1994, 77, 257.
13. B. Bernet, A. Vasella, Helv. Chim. Acta 2000, 83, 995.
14. A. Vasella, C. Witzig, R. Husi, Helv. Chim. Acta 1991, 74, 1362.
15. P. Deslongchamps, 'Stereoelectronic Effects in Organic Chemistry', Pergamon Press, Oxford, 1983.
16. P. Deslongchamps, Pure Appl. Chem. 1993, 65, 1161.
17. Z. Györgydeak, I.F. Pelyvas, 'Monosaccharide Sugars: Chemical Synthesis by Chain Elongation, Degradation and Epimerization', Academic Press, San Diego, 1998, p. 18-30.
18. B. M. Aebischer, H. W. Hanssen, A. T. Vasella, W. B. Schweizer, J. Chem. Soc., Perkin Trans. 1 1982, 2139.
19. G.V. Shustov, A. B. Zolotoi, N. L. Zaichenko, O. A. Dyachenko, L. O. Atovmyan, R. G. Kostyanovsky, Tetrahedron 1984, 40, 2151.
20. E. Schmitz, Angew. Chem. 1964, 76, 197.
21. R. Meuwly, A. Vasella, Helv. Chim. Acta 1986, 69, 25.
22. P. Uhlmann, E. Harth, A. B. Naughton, A. Vasella, Helv. Chim. Acta. 1994, 77, 2335.
23. L. Panza, A. Vasella, unpublished results.
24. T. Raiamannar, A. Vasella, unpublished results.
25. D. Beer, A. Vasella, Helv. Chim. Acta 1988, 68, 2254.
26. F. Baumberger, A. Vasella, Helv. Chim. Acta 1983, 66, 2210.
27. P. W. Austin, F. E. Hardy, J. G. Buchanan, J. Baddiley, J. Chem. Soc. 1965, 1419.
28. R. Barker, H. G. Fletcher, J. Org. Chem. 1961, 26, 4605.
29. R. Julina, A. Vasella, Helv. Chim. Acta 1985. 68, 819.
30. S. E. Mangholz, A. Vasella, Helv. Chim. Acta 1995, 78, 1020.
31. R. M. Adlington, A. G. M. Barrett, J. Chem. Soc., Perkin Trans 1 1981, 2848.
32. W. Timpe, K. Dax, N. Wolf, H. Weidmann, Carbohydr. Res. 1975, 39, 53.
33. F. A. Neugehauer, C. Krieger, H. Fischer, R. Siegel, Chem. Ber. 1983, 116, 2261.
34. F. A. Neugebauer, R. Siegel, Chem. Ber 1988, 118, 2157.
35. G. Maier, A. Schick, I. Bauer, R. Boese, M. Nussbaumer, Chem. Ber. 1992, 125, 2111.
36. C. M. Asselin, G. C. Fraser, H. K. Hall, W. E. Lindsell, A. B. Padias, P. N. Preston, J. Chem. Soc. Dalton Trans 1997, 3765.
37. M. Girardot, R. Nomak, J. K. Snyder, J. Org. Chem. 1998, 63, 10063.
38. S. Fritschi, A. Vasella, Helv. Chim. Acta 1991, 74, 2024.
39. J. Attenburrow, A. F. B. Cameron, J. H. Chapman, R. M. Evans, B. A. Hems, A. B. A. Jansen, T. Walker, J. Chem. Soc. 1952, 1094.
40. S. Koto, N. Morishima, Y. Miyata, S. Zen, Bull. Chem. Soc. Jpn. 1976, 49, 2639.
41. C. W. Holzapfel, R. Crous, Heterocycles 1998, 48, 1337.
42. Q. Meng, M. Hesse, Helv. Chim. Acta 1991, 74, 445.
43. Y. Rabinsohn, H. G. Fletcher Jr., J. Org. Chem. 1967, 32, 3452.