Abstract: The effects of microwave irradiation (2.45 GHz, 200 W) on glycosylation promoted by a solid super acid in supercritical carbon dioxide was investigated with particular attention paid to the structure of the acceptor substrate. Because of the symmetrical structure and high diffusive property of supercritical carbon dioxide, microwave irradiation did not alter the temperature of the reaction solution, but enhanced reaction yield when aliphatic acceptors are employed. Interestingly, the use of a phenolic acceptor under the same reaction conditions did not show these promoting effects due to microwave irradiation. In the case of aliphatic diol acceptors, the yield seemed to be dependent on the symmetrical properties of the acceptors. The results suggest that microwave irradiation do not affect the reactivity of the donor nor promoter independently. We conclude that the effect of acceptor structure on glycosylation yield is due to electric delocalization of hydroxyl group and dielectrically symmetric structure of whole molecule.
Keywords: glycosylation; microwave; super solid acid; supercritical carbon dioxide; dielectric constant; electric delocalization; symmetric structure
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Hinou, H.; Saito, N.; Ogawa, M.; Maeda, T.; Nishimura, S.-I. Microwave Effect for Glycosylation Promoted by Solid Super Acid in Supercritical Carbon Dioxide. Int. J. Mol. Sci. 2009, 10, 5285-5295.
Hinou H, Saito N, Ogawa M, Maeda T, Nishimura S-I. Microwave Effect for Glycosylation Promoted by Solid Super Acid in Supercritical Carbon Dioxide. International Journal of Molecular Sciences. 2009; 10(12):5285-5295.
Hinou, Hiroshi; Saito, Naohiro; Ogawa, Masato; Maeda, Takahiko; Nishimura, Shin-Ichiro. 2009. "Microwave Effect for Glycosylation Promoted by Solid Super Acid in Supercritical Carbon Dioxide." Int. J. Mol. Sci. 10, no. 12: 5285-5295.