Efficient regeneration of the 5-acetamido group of a neuraminic acid aryl glycoside from the O-nethyl acetimidate function under acidic conditions |
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Authors: | Orlova A V Zinin A I Kononov L O |
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Institution: | 1.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation ; |
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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. |
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