Carbohydrate Research 2006-07-24

On the nitrile effect in L-rhamnopyranosylation.

David Crich, Mitesh Patel

Index: Carbohydr. Res. 341(10) , 1467-75, (2006)

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Abstract

It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the beta-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.