Synthesis of vinyl glycosides and carbohydrate vinyl ethers from mixed acetals: a hetero-Diels–Alder approach to deoxygenated disaccharides

Treatment of mixed acetal glycosides as well as other types of carbohydrate mixed acetals with TMS-triflate and an amine base provides vinyl glycosides or carbohydrate vinyl ethers. Hetero-Diels–Alder reactions of carbohydrate 3- O- and 6- O-vinyl ethers with ethyl ( E)-ethoxymethylenepyruvate were...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2005-01, Vol.16 (1), p.273-282
Main Authors: Hughes, Kevin D., Nguyen, Tuan-Linh N., Dyckman, Damian, Dulay, Doreen, Boyko, Walter J., Giuliano, Robert M.
Format: Article
Language:English
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Summary:Treatment of mixed acetal glycosides as well as other types of carbohydrate mixed acetals with TMS-triflate and an amine base provides vinyl glycosides or carbohydrate vinyl ethers. Hetero-Diels–Alder reactions of carbohydrate 3- O- and 6- O-vinyl ethers with ethyl ( E)-ethoxymethylenepyruvate were carried out as part of a model study for the synthesis of deoxygenated disaccharides of antibiotics. A new method for the synthesis of vinyl glycosides and carbohydrate vinyl ethers is described. Mixed acetal glycosides and other types of carbohydrate mixed acetals are treated with TMS-triflate and an amine base, conditions developed by Gassman for the synthesis of enol ethers from acetals. The elimination proceeds regioselectively in most cases but also gives silyl ethers as side products in others. The hetero-Diels–Alder reactions of carbohydrate 3- O- and 6- O-vinyl ethers with ethyl ( E)-ethoxymethylenepyruvate were carried out as part of a model study for the synthesis of deoxygenated disaccharides of antibiotics.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2004.11.033