A. V. Orlova, A. Zinin, L. Kononov
Feb 1, 2009
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Journal
Russian Chemical Bulletin
Abstract
Treatment of protected N-acetylneuraminic acid 2-formyl-4-nitrophenyl glycoside with (diethyl-amino)sulfur trifluoride (DAST) and methanol resulted, apart from the known transformation of the formyl group into a difluoromethyl one, in an undocumented formation of 5-(O-methyl acetimidate) of Neu5Ac. This imidate was converted into the target 5-acetamido derivative under the action of aqueous TFA. The yield of the target product (94%) was twice as high as that reported earlier.