Abstract
A new oxo form of D-mannose with cyclohexylidene and benzyl protective groups is synthesized with the aim of adapting the chloroglycidate synthesis for natural 3-deoxy-D-manno-octulosonic acid. The sites of fixation of the protective groups were established by converting a model compound, 4-O-acetyl-2,3: 5,6-di-O-cyclohexylidene-aldehydo-D-mannose, into a known dicyclohexylidene-D-manno-furanose. The oxo form was reacted with methyl dichloroacetate to obtain a stereoisomeric mixture of chloroglycidates which were transformed into the corresponding pyruvate. The ketone and enol forms of the latter compound were isolated and separately characterized.
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