DOI:
10.1016/j.carres.2017.08.002
Author(s):
Kunj B. Mishra; Anand K. Agrahari; Vinod K. Tiwari
Tags:
Chemistry; Biochemistry, Genetics and Molecular Biology
article description
A controlled and facile synthesis of various glycosyl 1,3-oxazolidine-2-thiones and 1,3- thiozolidine-2-thiones has been accomplished from corresponding sugar azido alcohols utilizing Staudinger reaction (PPhand CS) via isothiocynate route. A series of reactions were performed to investigate the effects of CSand PPhon the selectivity of product formed. The excessive addition of CSwith PPh(1.2 equiv) afforded oxazolidine-2-thione alone, while the solitary addition of PPhfor 30 min followed by addition of CSto the reaction mixture resulted both the products in different ratios, which were successfully isolated using column chromatography (SiO). Furthermore, synthesis of 1,3-oxathiolan-2-imine from glycosyl epoxide has also been attempted. Structures of all the developed compounds have been elucidated using extensive spectroscopic techniques including IR, NMR and MS analysis.