الفهرس 
INTRODUCTIONOnly 14 pages are availabe for public view
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Abstract
6-Aryl-5-cyano-2-thiouracils (1a-c) were synthesized by base-catalyzed
condensation cyclization of ethyl cyanoacetate, thiourea, and aromatic aldehydes
in 45-52 % yields (Scheme 1).
6-Aryl-5-cyanouracils (2a-c) were synthesized by base-catalyzed
condensation cyclization of ethyl cyanoacetate, urea, and aromatic aldehydes in
40-45 % yields (Scheme 1).
6-Aryl-5-cyano-2-(methylsulfanyl)uracils (3a-c) were synthesized by
treatment of 6-aryl-5-cyano-2-thiouracils (1a-c) with methyl iodide and sodium
hydroxide in water and ethanol at 60 oC according to the method described by
Brown et al in 88-92 % yields (Scheme 1).Condensation of the sodium salt of the 6-aryl-5-cyano-2-
(methylsulfanyl)uracils (3a-c) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl
bromide (4) in dry DMF at 90 oC afforded 1-(2,3,4,6-tetra-O-acetyl-β-Dglucopyranosyl)-
6-aryl-5-cyano-2-(methylsulfanyl) pyrimidin-4(1H)-ones (5a-c)
in 78-83 % yields (Scheme 2).
Deacetylation of 5a-c in a mixture of methanol and ammonium hydroxide
(25 %) (1:1) at room temperature gave the free nucleosides 6a-c in 88-92 %
yields (Scheme 2).By the same way condensation of the sodium salt of the 6-aryl-5-cyano-2-
(methylsulfanyl)uracils (3a-c) with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl
bromide (7) in dry DMF at 90 oC afforded 1-(2,3,4,6-tetra-O-acetyl-β-Dgalactopyranosyl)-
6-aryl-5-cyano-2-(methylsulfanyl)-pyrimidin-4(1H)-ones
(8a-c) in 66-71 % yields (Scheme 3).Deacetylation of 8a-c in a mixture of methanol and ammonium hydroxide
(25 %) (1:1) at room temperature gave the free nucleosides 9a-c in 78-80 %
yields (Scheme 3).
GlucosylationGlucosylation of the sodium salt of the 6-aryl-5-cyanouracils (2a-c) with
2-acetamido-1-chloro-3,4,6-tri-O-acetyl-2-deoxy-D-glucose (10) in dry DMF at
90 oC gave the desired 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D