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2-Amino derivatives of levoglucosenone were prepared by reaction of the 2-methanesulfonyl (or p-toluenesulfonyl) derivatives with ammonia, methylamine, or octylamine under various conditions. The analogous reaction did not occur for saturated derivative 15. The 2-amino-3,4-dihydro derivative was prepared by catalytic hydrogenation of unsaturated amine 9.Amino sugars act as structural components of many natural compounds including such large groups as mucopolysaccharides and mixed biopolymers. However, they are rarely found in the free state. As a rule, amino sugars required for organic synthesis are obtained by aminolysis of halides, sulfonates, and anhydro derivatives of monosaccharides or reduction of ketose oximes and hydrazones [1,2]. The carbohydrate levoglucosenone (1), which is prepared by cellulose pyrolysis [3], is promising for preparing unsaturated amino sugars and their derivatives. N-Containing derivatives of this sugar enone include heterocyclic products of tandem conversions [4-7], oxime 2 [8], and regioisomeric amines formed by hydroxyamination of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose [9].Oxime 2 was synthesized by the literature method [8]. Furthermore, reaction of levoglucosenone with hydrazine sulfate in pyridine produced a different azomethine, hydrazone 3. Unfortunately, attempts to reduce azomethines 2 and 3 with LiAlH 4 gave products that were difficult to isolate from aqueous solutions.Alernative approaches could be based on substitution reactions, which are known to proceed difficultly in six-membered pyranose rings [1]. Nevertheless, keeping in mind the allylic position of the reaction center and the pseudoequatorial orientation of the substituted group, we studied the possibility of this approach.

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