On the nitrile effect in l-rhamnopyranosylation

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It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the β-selectivity of a number of l-rhamnopyranosylation reactions conducted by the thioglycoside method with activation by the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride couple. The use of more significant quantities of acetonitrile or propionitrile results in the formation of complex reaction mixtures containing little coupled product, but from which Ritter-type products can be isolated. © 2006 Elsevier Ltd. All rights reserved.




Crich, D., & Patel, M. (2006). On the nitrile effect in l-rhamnopyranosylation. Carbohydrate Research, 341(10), 1467–1475. https://doi.org/10.1016/j.carres.2006.03.036

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