Thioglycoside and trichloroacetimidate donors in regioselective glycosidations. Comparison with n-pentenyl glycosides

Tetrahedron Letters

Volumn 44, Issue 7, 2003, Pages 1417-1420

  López, J Cristóbal ^a   Gómez, Ana M ^a   Uriel, Clara ^a   Fraser Reid, Bert ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b Nat Prod Glycotechnology Res I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; THIOGLYCOSIDE; TRICHLOROACETIMIDIC ACID; TRISACCHARIDE;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; GLYCOSIDATION;

EID: 0037429018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02878-2     Document Type: Article

References (15)

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3. Fraser-Reid B., Anilkumar G.N., Nair L.G., Radhakrishnan K.V., Lopez J.C., Gomez A., Uriel C. Aust. J. Chem. 55:2002;123-130.
4. Konradsson P. Fraser-Reid B., Tatsuta K., Thiem J. Glycoscience: Chemistry and Chemical Biology. 1, Chapter 3.3.1:2001;Springer, Berlin.
5. Mootoo D.R., Konradsson P., Udodong U., Fraser-Reid B. J. Am. Chem. Soc. 110:1988;5583-5584.
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8. Nishimura S.-I. Fraser-Reid B., Tatsuta K., Thiem J. Chemical Biology and Biomedicine in 'Glycoscience'. 3, Chapter 6.5.1:2001;Springer, Berlin.
9. See for example: Schmidt R. R. In Modern Methods in Carbohydrate Synthesis; Khan, S. H.; O'Neil, R. A., Eds; Harwood Academic: The Netherlands, 1996; pp. 20-54 and references cited therein.
10. Wilson B.G., Fraser-Reid B. J. Org. Chem. 60:1995;317-320.
11. Paulsen H. Angew. Chem., Int. Ed. Engl. 21:1982;155-173.
12. 4 and concentrated. After work-up, the mixture was separated by flash chromatography to give the products.
13. 4 and concentrated. The mixture was purified by flash chromatography to give the products.
14. 2 (0.048 mmol) was added. The mixture was allowed to warm to 0°C. After 40 min, the reaction was quenched and processed as described for n-pentenylorthoesters.
15. 20: C, 71.19, H, 5.68. Found: C, 71.27, H, 5.73%.