Journal of Carbohydrate Chemistry p. 75 - 98 (1998)
Update date:2022-08-05
Topics:
Finizia, Gabriella
Carbamate derivatives of 3-aminodigitoxose (D-ristosamine) were prepared, with the purpose of synthesizing 3-amino-β-digitoxosyl derivatives of cardioactive steroids. A 1,3 participation procedure, used under acid or mercury salt catalysis, and the imidate procedure were investigated. A careful fine tuning of the glycosylation conditions was necessary in order to obtain significant β-D-stereoselectivity, which proved to be mainly dependent on the polarity of the solvent and the relative reactivity of the sugar and the nucleophile.
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