Abstract
Diamino 3a and 3b derivatives which obtained by Michael reaction were coupled with aldoses in the presence of acetic acid and I2 with stirring at room temperature gave 4, 5 and 6 respectively. Acetylation of compound 4 and 5 gave compound 7 and 8 respectively. Coupling of fructose with 3a and 3b in the presence or not of Con HCl gave compound 9 and 11 respectively. Acetylation of compound 9 with acetic anhydride and Pyridine gave compound 10. Some of the synthesized compounds have been screened as antibacterial and antifungal. The structures of the synthesized compounds have been deduced from their elemental analysis and spectral (IR, 1H-NMR) data.
Highlights
C-glycosides, wherein a carbon atom replaces the glycosidic oxygen have attracted considerable attention in carbohydrate and biological chemistry because of their stability [1] towards enzymatic acidic hydrolysis
C- glycosyl heteroaromatics were prepared from glycosyl donors such as glycosyl halides [7], hydroxides or O-glycosyl trichloroacetimidates using either the hetero aryl compounds in presence of lewis acids [8, 9]
The hot solution was poured onto crushed ice the formed acetate was filtered off and washed with water and dried afforded 10 as a white crystal yield 69%, m.p.200-201 ̊C
Summary
C-glycosides, wherein a carbon atom replaces the glycosidic oxygen have attracted considerable attention in carbohydrate and biological chemistry because of their stability [1] towards enzymatic acidic hydrolysis. In particular hexapyranosyl nucleosides as well as Cglycoconjugates bearing carbon linked nitrogen heterocycles have given rise to numerous synthetic and biological studies [2], due to their potential antiviral and antitumor activities. The reaction of C-centered nucleophiles with an activated and electrophilic C-glycosyl donor or glycal represents by far the most common approach, anomeric nucleophiles [6] and radical have been used to generate such compounds. C- glycosyl heteroaromatics were prepared from glycosyl donors such as glycosyl halides [7], hydroxides or O-glycosyl trichloroacetimidates using either the hetero aryl compounds in presence of lewis acids [8, 9]
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