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 language | Undefined/Unknown |
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Pages (from-to) | 8769–8772 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 130 |
Issue number | 27 |
DOIs | |
Publication status | Published - 2008 |
MoE publication type | A1 Journal article-refereed |