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Direct attachment of a carboxylate residue to nitrogen is not appropriate as the resulting carbamic acid would not be stable. The methylene bridge between the carboxylate and secondary nitrogen increases the distance between the carboxylate and anomeric carbon mimic by ∼1.1 Å relative to the C-COO- bond length for N-acetylneuraminic acid.
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Obtained by reduction of azide 12 to the amine with Raney nickel, N-acetylation, desilylation, and O-acetylation. X-ray: Abboud, K.; Parr, I. B.; Horenstein, B. A. Manuscript in prepration.
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