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

A1 Journal article (refereed)

Internal Authors/Editors

Publication Details

List of Authors: Roslund MU, Aitio O, Warna J, Maaheimo H, Murzin DY, Leino R
Publication year: 2008
Journal: Journal of the American Chemical Society
Journal acronym: J AM CHEM SOC
Volume number: 130
Issue number: 27
Start page: 8769
End page: 8772
Number of pages: 4
ISSN: 0002-7863


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.

Last updated on 2019-09-12 at 03:44