Two different protocols for the mild and selective acetolysis of 6-deoxysugar methyl disaccharides under thermodynamic or kinetic control have been developed. The structures of the disaccharides obtained depend on the protocol used and, in the kinetically controlled cases, on the 6-deoxysugar configuration and protecting group pattern too. The behavior of 6-deoxyhexose oligosaccharides of different series (rhamno, quinovo, and fuco) under these two reaction conditions has been studied and rationalized based on the competition between exo versus endo oxygen activation in the acetolysis mechanism.
Acetolysis of 6-deoxysugar disaccharide building-block: exo versus endo activation / L., Cirillo; Bedini, Emiliano; Parrilli, Michelangelo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2008), pp. 5704-5714.
Acetolysis of 6-deoxysugar disaccharide building-block: exo versus endo activation
BEDINI, EMILIANO;PARRILLI, MICHELANGELO
2008
Abstract
Two different protocols for the mild and selective acetolysis of 6-deoxysugar methyl disaccharides under thermodynamic or kinetic control have been developed. The structures of the disaccharides obtained depend on the protocol used and, in the kinetically controlled cases, on the 6-deoxysugar configuration and protecting group pattern too. The behavior of 6-deoxyhexose oligosaccharides of different series (rhamno, quinovo, and fuco) under these two reaction conditions has been studied and rationalized based on the competition between exo versus endo oxygen activation in the acetolysis mechanism.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
