Acyl group migration and cleavage in selectively protected beta-D-galactopyranosides as studied by NMR spectroscopy and kinetic calculations

MU Roslund, O Aitio, Johan Wärnå, H Maaheimo, Dmitry Murzin, Reko Leino

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Abstract

The migration of acetyl, pivaloyl, and benzoyl protective groups and their relative stabilities at variable pH for a series Of beta-D-galactopyranoses were studied by NMR spectroscopy. The clockwise and counterclockwise migration rates for the different ester groups were accurately determined by use of a kinetic model. The results presented provide new insights into the acid and base stabilities of commonly used ester protecting groups and the phenomenon of acyl group migration and may prove useful in the planning of synthesis strategies.
Original languageUndefined/Unknown
Pages (from-to)8769–8772
Number of pages4
JournalJournal of the American Chemical Society
Volume130
Issue number27
DOIs
Publication statusPublished - 2008
MoE publication typeA1 Journal article-refereed

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