Synthesis and intramolecular transesterifications of pivaloylated methyl alpha-D-galactopyranosides |
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Authors: | Petrović Vesna Tomić Srdanka Matanović Maja |
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Institution: | Department of Chemistry, Faculty of Science, University of Zagreb, Strossmayerov trg 14, Croatia. |
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Abstract: | Selective pivaloylations of methyl alpha-D-galactopyranoside have been studied under various reaction conditions. Partially pivaloylated products were submitted to additional acetylations. The structures were established by 1H and 13C NMR spectroscopies. Both, 2,6- and 3,6-dipivalates underwent intramolecular cyclization in neutral conditions (phosphate buffered saline, pH 7.2) to give a stable 2,3-orthoacid with a parallel 6-->4 migration of the pivaloyl group. |
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Keywords: | d-galactopyranosides" target="_blank">Methyl α-d-galactopyranosides acylated Pivalates intramolecular transesterifications |
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