Novel synthesis of 3-acetamido-3-deoxy- and 4-acetamido-4-deoxy-d-altrose from levoglucosenone using regioselective cis-oxyamination

Two rare amino sugars, 3-acetamido-3-deoxy- and 4-acetamido-4-deoxy-d-altrose, were prepared from levoglucosenone (1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranos-2-ulose) respectively by reduction of the carbonyl group, selective cis-oxyamination of the carbon-carbon double bond, detosylation of the p-toluenesulfonamido group, acetylation, acetolysis of the 1,6-anhydro bond, and finally deacetylation of the O-acetyl groups. The regioselectivity in cis-oxyamination of the carbon-carbon double bond of allylic alcohol obtained by reduction of levoglucosenone could be controlled by the choice of the protecting groups of the allylic hydroxyl group.