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

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)

Interna författare/redaktörer

Publikationens författare: Roslund MU, Aitio O, Warna J, Maaheimo H, Murzin DY, Leino R
Publiceringsår: 2008
Tidskrift: Journal of the American Chemical Society
Tidskriftsakronym: J AM CHEM SOC
Volym: 130
Nummer: 27
Artikelns första sida, sidnummer: 8769
Artikelns sista sida, sidnummer: 8772
Antal sidor: 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.

Senast uppdaterad 2019-09-12 vid 03:44