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

Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

62 Citeringar (Scopus)

Sammanfattning

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.
OriginalspråkOdefinierat/okänt
Sidor (från-till)8769–8772
Antal sidor4
TidskriftJournal of the American Chemical Society
Volym130
Utgåva27
DOI
StatusPublicerad - 2008
MoE-publikationstypA1 Tidskriftsartikel-refererad

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