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Synthesis Of Nucleosides Analogues Substituted With Oxy Amino Acetylenic Derivatives | ||
| Engineering and Technology Journal | ||
| Volume 25, Issue 6, 2007, Pages 702-710 PDF (142.41 K) | ||
| DOI: 10.30684/etj.25.6.2 | ||
| Author | ||
| 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 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. | ||
| Keywords | ||
| Nudeosides analogues; Amino acetylenic | ||
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