Microwave-accelerated Fischer glycosylation

Tetrahedron Letters

Volumn 46, Issue 20, 2005, Pages 3485-3488

  Bornaghi, Laurent F ^a   Poulsen, Sally Ann ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Fischer glycosylation; Glycosides; Microwave

Indexed keywords

ALCOHOL; ALLYL ALCOHOL; BENZYL ALCOHOL; GALACTOSE; GLUCOSE; GLYCOSIDE; MANNOSE; METHANOL; N ACETYLGALACTOSAMINE; N ACETYLGLUCOSAMINE;

ARTICLE; CHEMICAL REACTION KINETICS; FISCHER GLYCOSYLATION; GLYCOSYLATION; HEATING; MICROWAVE RADIATION; QUANTUM YIELD;

EID: 17844384197     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.126     Document Type: Article

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26. + resin (5.00 g). The reaction mixture was stirred at 70 °C for 8 h and then filtered. The filtrate was evaporated under reduced pressure. The residue was purified by recrystallisation from isopropanol. The desired methyl glycoside was isolated as a white solid (3.69 g, 68%). The product obtained has analytical data identical to the reference material described in the Spectral Database for Organic Compounds (SDBS) on http://www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_index.cgi
27. + resin (0.5 g). The reaction was carried out in a pressure tube, sealed with a Teflon septum. The pressure tube was introduced in the microwave oven for 10 min at 90 °C and then the reaction mixture filtered. The filtrate was evaporated under reduced pressure. The residue was purified by recrystallisation from isopropanol. The desired methyl glycoside was isolated as a white solid (0.33 g, 61%). When the reaction was carried out at 120 °C, 0.43 g of the glycoside was isolated (80%)
28. + resin (0.5 g). The reaction was carried out in a pressure tube, sealed with a Teflon septum. The pressure tube was introduced in the microwave oven for 10 min at 120 °C and then the reaction mixture filtered. The filtrate was evaporated under reduced pressure. The residue was purified by recrystallisation from methanol. The desired methyl glycoside was isolated as a white solid (0.39 g, 74%). The product obtained has analytical data identical to the reference material described in the Spectral Database for Organic Compounds (SDBS) on http://www.aist.go.jp/RIODB/SDBS/cgi- bin/cre_index.cgi
29. 1H NMR spectroscopy