Amino sugars isothiocyanic acid derivatives

Another main subject of research of Garcia Gonzalez, with the collaboration of J. Femandez-Bolanos, was the reaction of amino sugars with isothiocyanic acid derivatives. 2-Amino-2-deoxy-D-glucose hydrochloride and potassium thiocyanate were shown to give rise to 4-(D-arabino-tetritol-l-... 

The reaction of sugar isothiocyanates with aminosugars described above has also been studied with 1-amino (alkyl and arylamino)-l-deoxy-D-fructose 143 (Scheme 32). Thus, treatment of different 0-acylated sugar isoth-iocyanates with D-fructosamines 143 gave M-glycosyl-5-hydroxy-5-tetritolyl-imidazolidine-2-thiones 144 as pairs of diastereomers in almost quantitative yield [ 152]. The reaction times were shorter (15-20 min) for fructosamine or its M-methyl derivatives than in the cases of N-aryl derivatives (8-24 h). Acid-catalyzed dehydration of 144 with ethanolic TFA at rt led to 147 in 65-77% yield. These compounds can be considered simultaneously as M-nucleosides and acyclic C-nucleosides of imidazoline-2-thiones. 

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