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2,2-Dimethyl-4-(4-methoxy-phenoxy) butanoate and 2,2-dimethyl-4-azido butanoate: two new pivaloate-ester-like
Riccardo Castelli1, Herman S Overkleeft, Gijsbert A van der Marel
1Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Abstract:
The title compounds were developed to extend the available orthogonalities within the class of protecting groups removed by assisted cleavage. The mild, complementary (oxidative vs reductive) reaction conditions for the removal, together with their pivaloate-like character, were exploited, in combination with a levulinoyl-ester functioning as a third orthogonal protecting group, in the assembly of a Streptococcus mutans hexasaccharide built up from a oligorhamnose backbone featuring β-glucosyl appendages.
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