One-pot synthesis of oxazolidine-2-thione and thiozolidine-2-thione from sugar azido-alcohols.

Citation data:

Carbohydrate research, ISSN: 1873-426X, Vol: 450, Page: 1-9

Publication Year:
2017
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PMID:
28818771
DOI:
10.1016/j.carres.2017.08.002
Author(s):
Mishra, Kunj B; Agrahari, Anand K; Tiwari, Vinod K
Publisher(s):
Elsevier BV
Tags:
Chemistry; Biochemistry, Genetics and Molecular Biology
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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 (PPh and CS) via isothiocynate route. A series of reactions were performed to investigate the effects of CS and PPh on the selectivity of product formed. The excessive addition of CS with PPh(1.2 equiv) afforded oxazolidine-2-thione alone, while the solitary addition of PPh for 30 min followed by addition of CS to 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.