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Reaction of amino acids with d glycosyl iso thio cyanates and d gluconyl iso thio cyanates



Reaction of amino acids with d glycosyl iso thio cyanates and d gluconyl iso thio cyanates



Chemical & Pharmaceutical Bulletin (Tokyo) 27(5): 1137-1142



Reaction of glycosyl isothiocyanate (1a) with amino acids such as ethyl L-phenylalaninate hydrochloride, ethyl L-leucinate hydrochloride and ethyl .beta.-alaninate hydrochloride afforded glycosyl thioureides in good yields. Reaction of D-gluconyl isothiocyanate (1c) with amino acids (glycine, .beta.-alanine, GABA, .epsilon.-aminocaproic acid) or p-aminobenzoic acid gave the corresponding D-gluconamides and/or D-gluconyl thioureides. Treatment of 1a, b, c with 6-aminopenicillanic acid (6-APA) or ampicillin in the presence of triethylamine gave triethylammonium 6-(substituted thioureido)penicillanates and triethylammonium 6-(D-glycosyl thioureido)benzylpenicillanates. The reaction between 1c and phenacyl 6-APA afforded phenacyl 6-(D-gluconyl thioureido)penicillanate.

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