C-glycosides: A stereoselective synthesis of α-C-galactosamines with a glycosyl dianion

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 255-256

  Burkhart, Fred ^a   Kessler, Horst ^a  

^a Inst F Org Chem Biochem T   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSAMINE; GLYCOSIDE;

ARTICLE; CONFORMATION; DRUG SYNTHESIS; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0032518790     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10567-6     Document Type: Article

References (14)

1. 1 a) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
2. b) Postema, M. H. D. C-Glycoside Synthesis, CRC Press, 1995.
3. 2 Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J. M. Chem. Commun. 1996, 1883-1884 and references cited therein.
4. 3 Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347-348.
5. 4 a) Wittmann, V.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1993, 32, 1091-1093.
6. b) Frey, O.; Hoffmann, M.; Wittmann, V.; Kessler, H.; Uhlmann, P.; Vasella, A. Helv. Chim. Acta 1994, 77, 2060-2069.
7. c) Lesimple, P.; Beau, J. M. Bioorg. Med. Chem. 1994, 2, 1319-1330.
8. 5 a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067-6070.
9. b) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta, 1996, 79, 1519-1532.
10. c) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1997, 38, 1903-1906.
11. 6 a) Grundler, G.; Schmidt, R. R. Liebigs Ann. Chem. 1984, 1826-1847.
12. b) Briner, K.; Vasella, A. Helv. Chim. Acta, 1987, 70, 1341-1356.
13. 1-conformation. The coupling constant between H-1 and H-2 is approx. 2 Hz.
14. 8 The alkylated benzyl ether was determined by NMR spectroscopy using a HMBC spectrum.