Preparation of 2-amino-2,4-dideoxy-D-lyxo-hexopyranose (4-deoxy-D-mannosamine) from 1,6-anhydro-β-D-glucopyranose

Abstract

1,6-Anhydro-4-deoxy-2-O-p-toluenesulfonyl-β-D-xylo-hexopyranose (III), obtainable by a four-step synthesis from 1,6-anhydro-β-D-glucopyranose, was converted to 3-O-(N-benzylcarbamoyl) derivative V on reaction with benzyl isocyanate. The cyclization of V with sodium hydride in dimethylformamide gave a derivative of oxazolidin-2-one, VII, which on alkaline hydrolysis and hydrogenolysis gave the hydrochloride of 2-amino-1,6-anhydro-2,4-dideoxy-β-D-lyxo-hexopyranose (XI). When 1,6-anhydro derivative XI was treated with hydrochloric acid the hydrochloride of 2-amino-2,4-dideoxy-D-lyxo-hexopyranose (XIV) was obtained. Corresponding N-acetyl derivative XVI is suitable for studies of enzymatic synthesis of N-acetylneuraminic acid.