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https://www.readbyqxmd.com/read/15598075/thiosugar-nucleosides-synthesis-and-biological-activity-of-1-3-4-thiadiazole-thiazoline-and-thiourea-derivatives-of-5-thio-d-glucose
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Najim A Al-Masoudi, Yaseen A Al-Soud, Wasfi A Al-Masoudi
New acylated 5-thio-beta-D-glucopyranosylimino-disusbstituted 1,3,4-thiadiazols 8, and 11 were prepared, via spontaneous rearrangements, by cycloaddition of the glycosyl isothiocyanate 2 with the reactive intermediates 1-aza-2-azoniaallene hexachloroantimonates 4 and 6, respectively. Reaction of 2 with aminoacetone or chloroethylamine afforded the acylated 5-thio-beta-D-glucopyranosyl-4-imidazoline-2-thione nucleoside 16 and glucopyranosylamino-2-thiazoline derivative 18, respectively. Deblocking of 8, 11, 17 and 19 furnished the free nucleoside analogues 9, 12, 18 and 20, respectively...
2004: Nucleosides, Nucleotides & Nucleic Acids
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