Add time:08/02/2019         Source:sciencedirect.com

Publisher SummaryThis chapter presents the synthesis, chemistry, and preparative applications of monosaccharide isothiocyanates and thiocyanates. The ability of the isothiocyanate group to participate in nucleophilic reaction provides an attractive approach to nucleoside analogs and other nitrogen and sulfur heterocycles. Sugar thiocyanates are generally good precursors for the synthesis of thio and deoxy sugars and they are readily synthesized by a variety of methods from the corresponding halides. The thermodynamically more-stable isothiocyanate may also be formed by a secondary, isomerization reaction. It is found that that the treatment of semicarbazide with a nitroso acid at 0° affords the 1,2,3,4-thiatriazole derivative by addition and cyclization. The same 1,2,3,4-thiatriazole derivative 39 was obtained by the treatment of isothiocyanate 2 with hydrazoic acid. It is observed that isothiocyanate reacts with glycine, as well as with β-alanine, in tetrahydrofuran (THF) solution with the formation of corresponding N-(carboxyalky1)-d-gluconamides by nucleophilic attack of the amino group on the hard site, with simultaneous elimination of a molecule of thiocyanogen. The ability of aryl and alkyl isothiocyanates to react with reducing agents such as triethyl phosphite, triethylphosphine, or triphenyltin hydride to form the corresponding isocyanide is also elaborated in the chapter.

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