Author
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 was
converted to its 5-(2',3'-O-isopropylidene-b-D-ribofuranose) uracil (1), it
contains the free hydroxyl group at C-5 for the required chemical
modification. Accordingly (1) was prepared from 5-(b-D-ribofuranose) uracil
and acetone using anhydrous ferric chloride (FeCl3) as Lewis acid catalyst.
The treatment of (1) with propargyl bromide in benzene in a phase transfer
conditions in presence of tetrabutyl amonium bromide and 2% sodium
hydroxide solution yielded acetylenic ether derivative 5-(2',3'-Oisopropylidene-
5'-(propyn-2-yl) oxy-b-D-ribofuranose) uracil (2), which was
subjected to Mannich reaction with secondary aliphatic amines and
paraformaldehyde to give the acetylenic amino oxy derivatives (3a-f). The
treatment of (3a-f) with sulfuric acid at room temperature affected selectively
the 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 carbohydrate
derivatives containing acetylenic amines soluble in water, which possess a
possible biological activity.
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