Glycosyl transfer to nitrogen via cycloaddition

Organic Letters

Volumn 1, Issue 1, 1999, Pages 111-113

  Li, Baoqing ^a   Franck, Richard W ^a   Capozzi, Giuseppe ^b   Menichetti, Stefano ^b   Nativi, Cristina ^b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSIDE; NITROGEN; SULFUR;

ARTICLE; CHEMISTRY; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

GLUCOSIDES; GLYCOSYLATION; NITROGEN; STEREOISOMERISM; SULFUR;

EID: 0033564985     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990583l     Document Type: Article

References (17)

1. Varki, A. Glycobiology 1993, 3, 97-130.
2. (a) Bill, R. M.; Flitsch, S. L. Chem. Biol. 1996, 145.
3. (b) Paulsen, H.; Peters, S.; Bielfeldt, T. Glycoproteins; Montreuil, J., Schacter, H., Vliegenthart, J. F. G., Eds.; Elsevier: New York, 1995; Chapter 4, p 87.
4. Glycoconjugates resembling glycopeptides, but with "unnatural" inkers, are also an imponant area of research, for example: Rodriguez, E. Z.; Marcaurelle, L. A.; Bertozzi, C. R. J. Org. Chem. 1998, 63, 7134-7135.
5. Roberge, J. Y.; Beebe, X.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 3915-3927.
6. Schleyer, A.; Meldal, M.; Manat, R.; Paulsen, H.; Bock, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1976.
7. Ratcliffe, A. J.; Konradsson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1990 112, 5665.
8. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem. 1996, 108, 805-807; Angew. Chem., Int. Ed. Engl. 1996, 35, 777-779.
9. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem. 1996, 108, 805-807; Angew. Chem., Int. Ed. Engl. 1996, 35, 777-779.
10. (b) Dios, A.; Geer, A.; Marzabadi, C.; Franck, R. W. J. Org. Chem. 1998, 63, 6673.
11. Weinreb, S. M.; Ralbovsky, J. L. Trimethylsilyl ethanesulfonyl chloride. In Encylopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995; Vol. 7, pp 5255-5256.
12. Capozzi, G.; Menichetti, S.; Nativi, C.; Vergamini, C. Synthesis 1998, 915-918. Cycloadditions to simple dienophiles of an NOAc heterodiene related to 3c, and also prepared via retrocycloaddition.
13. Brown, C.; Hudson, R. F.; Record, K. A. F. J. Chem. Soc., Perkin Trans. 2 1978, 822-826.
14. Hamada, Y.; Kondo, Y.; Shibata, M.; Shioiri, T. J. Am. Chem. Soc. 1989, 101, 669-673
15. Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777.
16. All cycloadducts had molecular ions (either ESMS or CI/MS) and proton and carbon NMR data consistent with their structures. Adducts 7a, 8b, 10, and 11 have confirming combustion analyses and the structure of 7a has been confirmed by X-ray crystallography.
17. 2: C, 65.03; H, 5.56; N, 2.00. Found: C, 64.67; H, 5.93; N, 2.12.