Amino Acids and Amino Sugars from Bromodeoxyaldonolactones.

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Abstract
Treatment of 6-bromo-2,6-dideoxy-D-arabino hexono-1,4-lactone (1) with sodium azide in DMF gave the corresponding 6-azido lactone (2). Reduction yielded the 6-amino lactone, isolated as the 7-membered lactam (3) or as the 6-amino lactone hydrochloride (4). 2-Bromo-2,6-dideoxy-L-gluconolactone (5), with sodium azide in acetone, gave the 2-azido-2,6-dideoxy-L-mannonolactone (6), which was reduced with sodium borohydride to the azido sugar 7; finally, hydrogenation yielded 2-amino-2,6-dideoxy-L-mannose hydrochloride (8). Treatment of either 2,6-dibromo-2-,6-dideoxy-D-mannono- (9) or D-glucono-1,4-lactone (12) with sodium azide in acetone gave 2-azido-6-bromo-2,6-dideoxy-D-mannono-1,4-lactone (10). When 9, 10 or 12 was treated with sodium azide in DMF, 2,6-diazido-2,6-dideoxy-D-mannono-1,4-lactone (11) was formed. The azido lactones 10 and 11 were reduced to the corresponding sugars 13 and 14, respectively. Catalytic hydrogenation of 13 followed by hydrolysis gave 2-amino-2,6-dideoxy-D-mannose hydrocloride (15), whereas 14 by the same treatment gave 2,6-diamino-2,6-dideoxy-D-mannose dihydrochloride (17). The bromo lactones (9 and 12) were equilibrated in DMF with sodium bromide.
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