On the Synthesis of Aminoglycosides of Cardioactive Steroids: A Study Directed Towards β- Selective Glycosylations of 3-Aminodigitoxose with Digitoxigenin Analogues
作者:
Gabriella Finizia,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 1
页码: 75-98
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808005770
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
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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