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Selective Modifications Of Hydrophobic Vitamin B12 Derivatives At C-and D-positions.

Keith ó Proinsias, M. Giedyk, R. Loska, M. Chromiński, D. Gryko
Published 2011 · Chemistry, Medicine

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The acid-sensitivity of vitamin B(12) derived mono- and diamides was studied. It was found that the use of reductive ring-opening of the lactone moiety deactivated undesired decomposition of c-mono- and c,d-diamides under acidic conditions. As a result, reactions gave respectively c- or d-acids which were further functionalized via coupling with amino acids. Though mono- and diamides exhibited acid sensitivity, they were used for the preparation of several highly functionalized molecules showing their stability under various reaction conditions.
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