Organic compounds -- part of the class 532-570 series – Organic compounds – Azides
Patent
1988-09-09
1990-12-11
Griffin, Ronald W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azides
548225, 424 858, 514 8, C07C11700, C07F 718, C07F11706
Patent
active
049772864
ABSTRACT:
Novel, optically active azido alcohols are synthesized from N-haloacetyl oxazolidinone and are coupled with protected, activated carbohydrate residues in stereoselective glycosidic fashion to provide glycolipids in substantially pure stereochemical form. In accordance with certain preferred embodiments, the glycosphingolipids globotriaosylceramide, lactosyl ceramide, and galactosyl ceramide are synthesized in substantially pure stereochemical form from alkenyl, C-18 azido alcohols and protected fluoroglycosides and are employed as antigens in the production of antibodies useful, for example, in the treatment of disease.
REFERENCES:
patent: 3944574 (1976-03-01), Marsden et al.
patent: 4258199 (1981-03-01), Nicolaou et al.
patent: 4291166 (1981-09-01), Nicolaou et al.
Ito, Y. et al., Tetrahedron Lett., 1988, 29, 239.
Findeis, M. A. and Whitesides, G. M., J. Org. Chem., 1987, 52, 2838.
Julina, R. et al., Helv. Chimica Acta, 1986, 69, 368.
Roush, W. R. and Adam, M. A., J. Org. Chem., 1985, 50, 3752.
Schmidt, R. R. amd Zimmerman, P., Tetrahedron Lett., 1980, 27, 481.
Hakomori, S., Scientific American, 1986, 254, 254, 44.
Schmidt, R. R. and Klager, R., Anges, Chem. Int. Ed. Engl., 1985, 24, 65.
Schmidt, R. R. and Zimmermann, P., Angew. Chem. Int. Ed. Engl., 1986, 25, 725.
Nicolaou, K. C. et al., J. Am. Chem. Soc., 1984, 106, 4189.
Evans, D. A. et al., J. Am. Chem. Soc., 1981, 103, 3099.
Evans, D. A. amd Weber, A. E., J. Am. Chem. Soc., 1987, 109, 7151.
Abel-Magid, A. et al., J. Am. Chem. Soc., 1986, 108, 4595.
Caulfield Thomas J.
Nicolaou Kyriacos C.
Griffin Ronald W.
Trustees of the University of Pennsylvania
LandOfFree
Glycolipids does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Glycolipids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Glycolipids will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-391336