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A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors

El Ashry, El Sayed H ; El Tamany, El Sayed H ; Fattah, Mohy El Din Abdel ; Aly, Mohamed R E ; Boraei, Ahmed T A ; Duerkop, Axel



Zusammenfassung

Glycosylations of 5-(1H-indol-2-yl)-1,3,4-oxadiazoline-2(3H)-thione delivered various degrees of S- and/or N-glycosides depending on the reaction conditions. S- Glycosides were obtained regiospecifically by grinding oxadiazolinethiones with acylated alpha-D-glycosyl halides in basic alumina, whereas 3-N-(glycosyl)oxadiazolinethiones were selectively obtained by reaction with HgCl2 followed by ...

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