M. AL-Zahawyi Hala
Abstract
This work describes the synthesis of 5-(5'-(4-disubstituted amino-butyn-2-yl)oxy-b-D-ribofuranose) uracil.For the synthesis of these compounds, 5-(b-D-ribofuranose) uracil wasconverted ...
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This work describes the synthesis of 5-(5'-(4-disubstituted amino-butyn-2-yl)oxy-b-D-ribofuranose) uracil.For the synthesis of these compounds, 5-(b-D-ribofuranose) uracil wasconverted to its 5-(2',3'-O-isopropylidene-b-D-ribofuranose) uracil (1), itcontains the free hydroxyl group at C-5 for the required chemicalmodification. Accordingly (1) was prepared from 5-(b-D-ribofuranose) uraciland acetone using anhydrous ferric chloride (FeCl3) as Lewis acid catalyst.The treatment of (1) with propargyl bromide in benzene in a phase transferconditions in presence of tetrabutyl amonium bromide and 2% sodiumhydroxide solution yielded acetylenic ether derivative 5-(2',3'-Oisopropylidene-5'-(propyn-2-yl) oxy-b-D-ribofuranose) uracil (2), which wassubjected to Mannich reaction with secondary aliphatic amines andparaformaldehyde to give the acetylenic amino oxy derivatives (3a-f). Thetreatment of (3a-f) with sulfuric acid at room temperature affected selectivelythe removal of acetal group at 2',3'-position giving (4a-f) in good yield.The aim of the present work is the preparation of new carbohydratederivatives containing acetylenic amines soluble in water, which possess apossible biological activity.
