On the synthesis of aminoglycosides of cardioactive steroids: A study directed towards β-selective glycosylations of 3-aminodigitoxose with digitoxigenin analogues

Article abstract of DOI:10.1080/07328309808005770

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.

Full text of DOI:10.1080/07328309808005770

Journal of Carbohydrate Chemistry
ISSN: 0732-8303 (Print) 1532-2327 (Online) Journal homepage: http://www.tandfonline.com/loi/lcar20
On the Synthesis of Aminoglycosides of
Cardioactive Steroids: A Study Directed Towards β-
Selective Glycosylations of 3-Aminodigitoxose with
Digitoxigenin Analogues
Gabriella Finizia
To cite this article: Gabriella Finizia (1998) On the Synthesis of Aminoglycosides of Cardioactive
Steroids: A Study Directed Towards β- Selective Glycosylations of 3-Aminodigitoxose
with Digitoxigenin Analogues, Journal of Carbohydrate Chemistry, 17:1, 75-98, DOI:
10.1080/07328309808005770
To link to this article: http://dx.doi.org/10.1080/07328309808005770
Published online: 16 Aug 2006.
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Date: 18 June 2016, At: 16:09