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

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

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 α-D-glycosyl halides in basic alumina, whereas 3-N-...

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Bibliographic Details
Main Authors: El Sayed H. El Ashry, El Sayed H. El Tamany, Mohy El Din Abdel Fattah, Mohamed R. E. Aly, Ahmed T. A. Boraei, Axel Duerkop
Format: Article
Language:English
Published: Beilstein-Institut 2013-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
glycosyloxadiazolinethiones
glycosylsulfanyloxadiazoles
glycosylthiosemicarbazides
thermal rearrangement
X-ray crystallography
Online Access:https://doi.org/10.3762/bjoc.9.16

Internet

https://doi.org/10.3762/bjoc.9.16

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