A new method testing the orthogonality of different protecting groups

•A method was developed to identify orthogonality of various protecting groups.•The method is based on the chemo-selectivity of protecting groups.•The crude reaction mixtures were analysed by HPLC.•With the method a new deprotection protocol for the propagyl group is developed. [Display omitted] A n...

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Bibliographic Details
Published in:Carbohydrate research 2015-12, Vol.418, p.98-103
Main Authors: Ágoston, Károly, Ágoston, Ágnes, Dorgan, Colin R., Fügedi, Péter
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Chromatography, High Pressure Liquid - methods
Glucosides - chemical synthesis
Glucosides - chemistry
Method development
Molecular Conformation
Orthogonal protection
Protecting groups
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Summary:•A method was developed to identify orthogonality of various protecting groups.•The method is based on the chemo-selectivity of protecting groups.•The crude reaction mixtures were analysed by HPLC.•With the method a new deprotection protocol for the propagyl group is developed. [Display omitted] A new test was elaborated to identify a new set of orthogonal protecting groups. With the developed method eight different protecting groups were tested under various deprotection conditions and the complex reaction mixtures were analysed by HPLC. The developed method allows for quick identification of orthogonality using simple model structures.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2015.10.007