Formation of anomeric phosphodiester linkages using H-phosphonate acceptors

A new way of constructing anomeric glycosyl phosphodiester linkages has been explored. Non-anomeric monosaccharide hydrogen phosphonate monoesters ( 5 and 9) have been used as acceptors in couplings using various benzylated galactosyl donors (trichloroacetimidate, thioglycoside, bromo and chloro sug...

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Bibliographic Details
Published in:Tetrahedron letters 1999-04, Vol.40 (15), p.3049-3052
Main Authors: Garegg, Per J., Hansson, Jonas, Helland, Anne-Charlotte, Oscarson, Stefan
Format: Article
Language:English
Subjects:
Carbohydrates
Coupling reactions
Phosphorous acid and derivatives
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Summary:A new way of constructing anomeric glycosyl phosphodiester linkages has been explored. Non-anomeric monosaccharide hydrogen phosphonate monoesters ( 5 and 9) have been used as acceptors in couplings using various benzylated galactosyl donors (trichloroacetimidate, thioglycoside, bromo and chloro sugars, 1–4, 7 and 8) and promoters to give, after oxidation, good yields of phosphodiester linked “disaccharides” ( 6 and 10), products usually obtained by using an anomeric hydrogen monophosphonate, a hydroxyl acceptor and pivaloyl chloride as coupling reagent. Saccharide hydrogen phosphonate monoesters have been used as acceptors in couplings with various types of glycosyl donors and promoters to give phosphodiester linked “disaccharides” in good yield after oxidation.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00362-7