Preparation of glycosyl fluorides from phenyl 1-seleno- and phenyl 1-telluroglycosides

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8697-8700

  Horne, Graeme ^a,b   Mackie, William ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b University of Bath   (United Kingdom)

Author keywords

Glycosides; Neighbouring group effects; Selenium; Selenium compounds; Solvent effects; Solvents

Indexed keywords

GLYCOSIDE; GLYCOSYL FLUORIDE; ION; SELENIUM; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033521089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01846-8     Document Type: Article

References (15)

1. Shimizu, M.; Togo, H.; Yokoyama, M. Synthesis 1998, 6, 799.
2. Fluorinated carbohydrates; Taylor, N. F., Ed.; ACS Symposium Series; Washington, DC, 1988; 374.
3. Glaudemans, C. P. J.; Kovac, P.; Nashed, E. M.; Padlan, E. A.; Arepelli, S. R. In Synthetic oligosaccharides; Kovac, P., Ed.; ACS Symposium Series; Washington, DC, 1994; 560, 157.
4. Phenyl 2-azido-2-deoxy-1-seleno-α-D-glycopyranosides were prepared according to the method of Czernecki, S. E.; Randriamandimby, D. Tetrahedron Lett. 1993, 34, 7915. Phenyl -selenoglycosides were prepared according to the methodof Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269.
5. Phenyl 2-azido-2-deoxy-1-seleno-α-D-glycopyranosides were prepared according to the method of Czernecki, S. E.; Randriamandimby, D. Tetrahedron Lett. 1993, 34, 7915. Phenyl 1-selenoglycosides were prepared according to the method of Mehta, S.; Pinto, B. M. J. Org. Chem. 1993, 58, 3269.
6. Stick, R. V.; Matthew, D.; Tilbrook, G.; Williams, S. J. Aust. J. Chem. 1997, 50, 233.
7. Caddick, S.; Gazzard, L.; Motherwell, W. B.; Wilkinson, J. A. Tetrahedron 1996, 52, 149.
8. Motherwell, W. B., personal communication, 1996.
9. Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L. J. Am. Chem. Soc. 1984, 106, 4189.
10. Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
11. Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Pergamon Press: Oxford, 1990.
12. 4) and concentrated in vacuo. The crude residue was purified on a short silica gel column to yield the corresponding glycosyl fluorides.
13. Braccini, I.; Derouet, C.; Esnault, J.; Du Penhoat, C. H.; Mallet, J. M.; Michon, V.; Sinay, P. Carbohydr. Res. 1993, 246, 23.
14. Ratcliffe, A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1990, 747.
15. Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157.