Reaction of amino sugars with malondialdehyde

Article abstract of DOI:10.1016/0008-6215(90)84188-Z

2-Amino-2-deoxy-D-glucose hydrochloride reacted with the sodium salts of malondialdehyde (7) and methylmalondialdehyde (8) to give 2-deoxy-2-<(3-oxo-1-propen-1-yl)amino>-α,β-D-glucopyranose (12) and 2-deoxy-2-<(2-methyl-3-oxo-1-propen-1-yl)amino>-α,β-D-glucopyranose (13), respectively, in good yields.Likewise, β-D-glucopyranosylamine gave 3-(β-D-glucopyranosylamino)-2-propenal (14) and 3-(β-D-glucopyranosylamino)-2-methyl-2-propenal (15). 2-Amino-2-deoxy-β-D-glucopyranose and 7 reacted at pH ca. 9 to give a mixture of 3-pyrrolecarbaldehyde (19), 5-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde (21), and 5-(α,β-D-erythrofuranosyl)-3-pyrrolecarbaldehyde (20αβ).The Na salt of crude 1 is usually contaminated with 2,4-diformyl-3-(2,2-dimethoxyethyl)glutaraldehyde (9) and 2,4-diformyl-3-methylglutaraldehyde (10), so that, in its reactions with 2-amino-2-deoxy-D-glucose hydrochloride, 2-deoxy-2-<3,5-diformyl-4-(2,2-dimethoxyethyl)-1,4-dihydropyridin-1-yl)-α,β-D-glucopyranose (16) and 2-deoxy-2-(3,5-diformyl-4-methyl-1,4-dihydropyridin-1-yl)-α,β-D-glucopyranose (17) were produced in addition to 12.Likewise, with β-D-glucopyranosylamine, it afforded 14 and 3,5-diformyl-1-β-D-glucopyranosyl-4-(2,2-dimethoxyethyl)-1,4-dihydropyridine (18).Compounds 16 and 17 were obtained also by the reaction of 2-amino-2-deoxy-D-glucose hydrochloride with 9 and 10, respectively.