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- W2024366258 abstract "Abstract The oxime ( 2 ) of 1,6-anhydro-3,4- O -isopropylidene-β- D - lyxo -hexopyranos-2-ulose ( 1 ) in aqueous hydrochloric acid is reduced stereospecifically by hydrogen and a platinum catalyst, with concomitant hydrolysis of the O -isopropylidene group, to give 2-amino-1,6-anhydro-2-deoxy-β- D -talopyranose hydrochloride ( 3 ) in high yield. Hydrolysis of the anhydro sugar 3 under more vigorous conditions gave crystalline 2-amino-2-deoxy-α- D -talopyranose hydrochloride ( 4 ). In aqueous solution, the amino sugar 4 exists as a 1:2 mixture of the α and β- D -pyranose anomers. Reduction of 1,6-anhydro-2,3- O -isopropylidene-β- D - lyxo -hexopyranos-4-ulose oxime ( 5 ) in aqueous hydrochloric acid, with hydrogen over platinum, also occurred stereospecifically, to give a crystalline product formulated as 4-amino-1,6-anhydro-4-deoxy-β- D -talopyranose hydrochloride ( 6 ), which was further characterized as the peracetylated derivative 7 . Attempted hydrolysis of 6 to give 4-amino-4-deoxy- D -talose hydrochloride ( 8 ) gave only unchanged 6 and tarry products, presumably because the free 4-amino sugar derivative 8 undergoes rapid destruction in the acid solution by way of a pyrrole derivative." @default.
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- W2024366258 date "1968-06-01" @default.
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- W2024366258 title "Synthesis of 1,6-anhydro derivatives of 2-amino-2-deoxy-β-D-talopyranose and 4-amino-4-deoxy-β-D-talopyranose" @default.
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