Oximes, Hydroxylamines and Nitrones

An improved synthesis of the oximino-lactone derivative 63 ( PUGNAc ) in five steps from 2-acetamido-2-deoxy-a-D-glucopyranose tetraacetate has been described, the critical step being a low temperature oxidation of an acyclic aldose oxime intermediate to a cyclic oximino-lactone with NCS and DBU. The D-xylono-l,5-lacatam oxime derivative 64 has been synthesized from an L-serinal derivative as a potential A-acetylglucosaminyl transferase inhibitor.  

Glycosylamines produced by reaction of unprotected sugars (e.g. LacNAc, Le trisaccharide and sialyl-Le tetrasaccharide) with the photoreactive, carbene- 

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